4-haloalkyl-3-heterocyclylpyridines, 4-haloalkyl-5-heterocyclyl-pyrimidines and 4-trifluoromethyl-3-oxadiazolylpyridines, processes for their preparation, compositions comprising them, and their use as pesticides

ABSTRACT

The present invention relates to 4-Haloalkyl-3-heterocyclylpyridines, 4-haloalkyl-5-heterocyclyl-pyrimidines and 4-trifluoromethyl-3-oxadiazolylpyridines, Processes for Their Preparation, Compositions Comprising Them, and Their Use as Pesticides 
     More particularly, the present invention relates to 4-trifluoromethyl-3-oxadiazolylpyridines of the formula (I′), to processes for their preparation, to compositions comprising them and to the use of these compounds for controlling animal pests, in particular insects, spider mites, ectoparasites and helminths:                    
     wherein X, Y are as defined in the description.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a continuation-in-part of U.S. application Ser. No. 09/808,194, filed on Mar. 14, 2001, now U.S. Pat. No. 6,521,610, which is a divisional application of U.S. application Ser. No. 09/096,748, filed on Jun. 12, 1998, now U.S. Pat. No. 6,239,160, and claims the benefit of priority to DE 19725450, filed on Jun. 16, 1997. This application is also a continuation-in-part of U.S. application Ser. No. 09/461,792, filed on Dec. 15, 1999, now abandoned, and claims benefit of priority to DE 19858193.9, filed on Dec. 17, 1998.

FIELD OF THE INVENTION

The present invention relates to 4-haloalkyl-3-heterocyclylpyridines and 4-haloalkyl-5-heterocyclylpyrimidines, to processes for their preparation, to compositions comprising them and to the use of novel and known 4-haloalkyl-3-heterocyclylpyridines and 4-haloalkyl-5-heterocyclylpyrimidines for controlling animal pests, in particular insects, spider mites, ectoparasites and helminths. More particularly, the invention relates to 4-trifluoromethyl-3-oxadiazolylpyridines, to processes for their preparation, to compositions comprising them and to their use for controlling animal pests, in particular insects, spider mites, ectoparasites and helminths.

BACKGROUND OF THE INVENTION

It is already known that appropriately substituted pyridines or pyrimidines have acaricidal and insecticidal activity. Thus, WO 95/07891 describes pyridines which carry a cycloalkyl radical in position 4 which is linked via a hetero atom and a group of various substituents in position 3. WO 93/19050 discloses 4-cycloalkylamino- and 4-cycloalkoxypyrimidines which carry in position 5 inter alia alkyl, alkoxy or haloalkoxy groups. However, the desired activity against the harmful organisms is not always sufficient. Additionally, these compounds often have undesirable toxicologic properties toward mammals and aquatic living beings.

Pyridyl-1,2,4-thiadiazoles having fungicidal properties are described in DE-A 42 39 727. The compounds disclosed therein carry the thiadiazole ring in position 2, 3 or 4 of the unsubstituted pyridine.

WO-A-98/57969, which is not prepublished, proposes 4-haloalkylpyridines and -pyrimidines for use as pesticides.

EP-A 0 371 925 discloses some 1,3,4-oxadiazolyl- and 1,3,4-thiadiazolyl-pyrimidines having nematicidal and fungicidal properties. In the biologically effective compounds disclosed in this publication, the pyrimidine carries the oxadiazolyl or thiadiazolyl ring either

a) in position 5 and is optionally substituted by a thiomethyl group in position 2, or

b) in position 2 and is optionally substituted in position 4 and 6, in each case by a methyl group.

Aryltriazole derivatives for use as pesticides are known from EP-A 0 185 256. In addition to the phenyltriazoles, which are particularly preferred, three haloalkyl-3-pyridyltriazoles are disclosed:

3-(2-chlorophenyl)-1-methyl-5-(4-trifluoromethyl-3-pyridyl)-1H-1,2,4-triazole

3-(2,6-difluorophenyl)-1-methyl-5-(4-trifluoromethyl-3-pyridyl)-1H-1,2,4-triazole and

3-(2-chloro-4-fluorophenyl)-1-methyl-5-(4-trifluoromethyl-3-pyridyl)-1H-1,2,4-triazole,

their desired activity at low application rates, however, is not always satisfactory, especially when controlling insects and spider mites.

Some commercially available 4-haloalkyl-3-heterocyclylpyridines are known from the Maybridge Catalogue 1996/1997, Maybridge Chemical CO. LTD., Trevillett Tintagel, GB:

3-(3,5-dichlorophenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

5-(4-trifluoromethyl-3-pyridyl)-3-phenyl-1,2,4-oxadiazole

3-(4-trifluoromethyl-3-pyridyl)-5-phenyl-1,2,4-oxadiazole

5-(2-chlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

5-(3-chlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

5-(4-chlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

5-(2-fluorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

5-(4-fluorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

5-(2,4-dichlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

5-(3,4-dichlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

5-(3,5-dichlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

5-(2,6-dichloro-4-pyridyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

5-(3,5-bistrifluoromethylphenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

2-(2-chlorophenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazole

2-(3-chlorophenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazole

2-(4-chlorophenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazole

2-(2-trifluoromethoxyphenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazole

2-(4-trifluoromethoxyphenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazole

2-(4-trifluoromethyl-3-pyridyl)-5-phenyl-1,3,4-oxadiazole

2-(4-trifluoromethyl-3-pyridyl)-4-methylthiazolecarbohydrazide

ethyl 2-(4-trifluoromethyl-3-pyridyl)-4-methylthiazolecarboxylate

N-(4-chlorophenyl)carbonyl-N′-[2-(4-trifluoromethyl-3-pyridyl)-4-methyl-5-thiazolyl]carbonylhydrazine

2-(4-trifluoromethyl-3-pyridyl)-4-thiazolecarbohydrazide

4-(4-chlorophenyl)-2-(4-trifluoromethyl-3-pyridyl)thiazole

4-(4-cyanophenyl)-2-(4-trifluoromethyl-3-pyridyl)thiazole

N-(4-trifluoromethylphenyl)carbonyl-N′-[2-(4-trifluoromethyl-3-pyridyl)-4-thiazolyl]carbonylhydrazine

2-(2-(4-trifluoromethyl-3-pyridyl)thiazolyl)-5-chloro-3-methylbenzo[b]thiophene

2-(4-chlorophenylmethylthio)-5-(4-trifluoromethyl-3-pyridyl)-1-methyl-1H-1,3,4-triazole

2-(4-chlorophenylcarbonylmethylthio)-5-(4-trifluoromethyl-3-pyridyl)-1-methyl-1H-1,3,4-triazole and

2-ethoxycarbonylmethylthio-5-(4-trifluoromethyl-3-pyridyl)-1-methyl-1H-1,3,4-triazole.

However, a biological activity toward harmful organisms has hitherto not been disclosed.

SUMMARY OF THE INVENTION

It is an object of the present invention to provide compounds having good insecticidal and acaricidal properties and simultaneously low toxicity toward mammals and aquatic living beings.

DETAILED DESCRIPTION OF THE INVENTION

It has now been found that compounds of the formula I, optionally as salts, have a wider activity spectrum against animal pests and simultaneously more favorable toxicologic properties toward mammals and aquatic living beings than the prior art compounds.

In the formula (I):

Y is halo-C₁-C₆-alkyl;

X is CH or N;

m is 0 or 1;

Q is a 5-membered heterocyclic group

in which

a) X¹ = W, X² = NR^(a), X³ = CR^(b)R¹ or b) X¹ = NR^(a), X² = CR^(b)R¹, X³ = W or c) X¹ = V, X² = CR^(a)R¹, X³ = NR^(b) or d) X¹ = V, X² = CR^(a)R², X³ = CR^(b)R³ or e) X¹ = V, X² = CR⁴R⁵, X³ = CR⁶R⁷ or f) X¹ = NR^(a), X² = CR^(b)R¹, X³ = NR⁸;

R^(a) and R^(b) together are a bond

V is oxygen, sulfur or NR⁹;

W is oxygen or sulfur;

R¹ is hydrogen,

(C₁-C₂₀)-alkyl, (C₂-C₂₀)-alkenyl, (C₂-C₂₀)-alkynyl, (C₃-C₈)-cycloalkyl,

(C₄-C₈)-cycloalkenyl, (C₆-C₈)-cycloalkynyl,

where the six last-mentioned radicals are optionally substituted by one or more radicals from the group

halogen, cyano, nitro, hydroxyl, —C(═W)R¹⁰, —C(═NOR¹⁰)R¹⁰, —C(═NNR¹⁰ ₂)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —OC(═W)R¹⁰, —OC(═W)OR¹⁰, —NR¹⁰C(═W)R¹⁰, —N[C(═W)R¹⁰]₂, —NR¹⁰C(═W)OR¹⁰, —C(═W)NR¹⁰—NR¹⁰ ₂, —C(═W)NR¹⁰—NR¹⁰[C(═W)R¹⁰], —NR¹⁰—C(═W)NR¹⁰ ₂, —NR¹⁰—NR¹⁰C(═W)R¹⁰, —NR¹⁰—N[C(═W)R¹⁰]₂, —N[(C═W)R¹⁰]—NR¹⁰ ₂, —NR¹⁰—NR¹⁰[(C═W)R¹⁰], —NR¹⁰—NR¹⁰[(C═W)WR¹⁰], —NR¹⁰—R¹⁰[(C═W)NR¹⁰ ₂], —NR¹⁰(C═NR¹⁰)R¹⁰, —NR¹⁰(C═NR¹⁰)NR¹⁰ ₂, —O—NR¹⁰ ₂, —O—NR¹⁰(C═W)R¹⁰, —SO₂NR¹⁰ ₂, —NR¹⁰SO₂R¹⁰, —SO₂OR¹⁰, —OSO₂R¹⁰, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SiR¹⁰ ₃, —SeR¹⁰, —PR¹⁰ ₂, —P(═W)R¹⁰ ₂, —SOR¹⁰, —SO₂R¹⁰, —PW₂R¹⁰ ₂, —PW₃R¹⁰ ₂, aryl and heterocyclyl,

the two last-mentioned radicals optionally being substituted by one or more radicals from the group

(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl, (C₆-C₈)-cycloalkynyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-haloalkynyl, halogen, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SiR¹⁰ ₃, —C(═W)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —SOR¹⁰, —SO₂R¹⁰, nitro, cyano and hydroxyl,

aryl,

which is optionally substituted by one or more radicals from the group

(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl and (C₆-C₈)-cycloalkynyl,

where these six abovementioned radicals are optionally substituted by one or more radicals from the group

halogen, cyano, nitro, —C(═W)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SOR¹⁰ and —SO₂R¹⁰,

halogen, cyano, nitro, —C(═W)R¹⁰, —C(═NOR¹⁰)R¹⁰, —C(═NNR¹⁰ ₂)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —OC(═W)R¹⁰, —OC(═W)OR¹⁰, —NR¹⁰C(═W)R¹⁰, —N[C(═W)R¹⁰]₂, —NR¹⁰C(═W)OR¹⁰, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SiR¹⁰ ₃, —PR¹⁰ ₂, —SOR¹⁰, —SO₂R¹⁰, —PW₂R¹⁰ ₂ and —PW₃R¹⁰ ₂,

heterocyclyl,

which is optionally substituted by one or more radicals from the group

(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl and (C₆-C₈)-cycloalkynyl,

where the six abovementioned radicals are optionally substituted by one or more radicals from the group

cyano, nitro, halogen, —C(═W)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —NR¹⁰C(═W)R¹⁰, —N[C(═W)R¹⁰]₂, —OC(═W)R¹⁰, —OC(═W)OR¹⁰, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SOR¹⁰ and —SO₂R¹⁰;

halogen, cyano, nitro, —C(═W)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —OC(═W)R¹⁰, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SOR¹⁰ and —SO₂R¹⁰;

—OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SOR¹⁰, —SO₂R¹⁰, —C(═W)R¹⁰, —C(═NOR¹⁰)R¹⁰, —C(═NNR¹⁰ ₂)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —OC(═W)R¹⁰, —OC(═W)OR¹⁰, —NR¹⁰C(═W)R¹⁰, —N[C(═W)R¹⁰]₂, —NR¹⁰C(═W)OR¹⁰, —C(═W)NR¹⁰—NR¹⁰ ₂, —C(═W)NR¹⁰—NR¹⁰[C(═W)R¹⁰], —NR¹⁰—C(═W)NR¹⁰ ₂, —NR¹⁰—NR¹⁰C(═W)R¹⁰, —NR¹⁰—NC(═W)R¹⁰ ₂, —N(C═W)R¹⁰—NR¹⁰ ₂, —NR¹⁰—NR¹⁰[(C═W)R¹⁰], —NR¹⁰—NR¹⁰[(C═W)WR¹⁰], —NR¹⁰—NR¹⁰[(C═W)NR¹⁰ ₂], —NR¹⁰(C═NR¹⁰)R¹⁰, —NR¹⁰(C═NR¹⁰)NR¹⁰ ₂, —O—NR¹⁰ ₂, —O—NR¹⁰(C═W)R¹⁰, —SO₂NR¹⁰ ₂, —NR¹⁰SO₂R¹⁰, —SO₂OR¹⁰, —OSO₂R¹⁰, —SC(═W)R¹⁰, —SC(═W)OR¹⁰, —SC(═W)R¹⁰, —PR¹⁰ ₂, —PW₂R¹⁰ ₂, —PW₃R¹⁰ ₂, SiR¹⁰ ₃ or halogen;

R² and R³ independently of one another have the definitions given in R¹;

R² and R³ together form a 5- to 7-membered ring which may be partially or fully unsaturated and may be interrupted by one or more atoms from the group nitrogen, oxygen and sulfur, the oxygen atoms not being directly adjacent to one another, and the ring optionally being substituted by one or more, but at most 5, radicals R¹;

R⁴ and R⁶ independently of one another have the definitions given in R¹;

R⁴ and R⁶ together form a 4- to 7-membered ring which may be partially or fully unsaturated and may be interrupted by one or more atoms from the group nitrogen, oxygen and sulfur, the oxygen atoms not being directly adjacent to one another, and the ring optionally being substituted by one or more, but at most 5, radicals R¹;

R⁵ and R⁷ independently of one another are hydrogen,

(C₁-C₂₀)-alkyl, (C₂-C₂₀)-alkenyl, (C₂-C₂₀)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl, (C₆-C₈)-cycloalkynyl,

where the six last-mentioned radicals are optionally substituted by one or more radicals from the group

halogen, cyano, nitro, hydroxyl, —C(═W)R¹⁰, —C(═NOR¹⁰)R¹⁰, —C(═NNR¹⁰ ₂)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —OC(═W)R¹⁰, —OC(═W)OR¹⁰, —NR¹⁰C(═W)R¹⁰, —N[C(═W)R¹⁰]₂, —NR¹⁰C(═W)OR¹⁰, —C(═W)NR¹⁰—NR¹⁰ ₂, —C(═W)NR¹⁰—NR¹⁰[C(═W)R¹⁰], —NR¹⁰—C(═W)NR¹⁰ ₂, —NR¹⁰—NR¹⁰C(═W)R¹⁰, —NR¹⁰—N[C(═W)R¹⁰]₂, —N[(C═W)R¹⁰]—NR¹⁰ ₂, —NR¹⁰—NR¹⁰[(C═W)R¹⁰], —NR¹⁰—NR¹⁰[(C═W)WR¹⁰], —NR¹⁰—NR¹⁰[(C═W)NR¹⁰ ₂], —NR¹⁰(C═NR¹⁰)R¹⁰, —NR¹⁰(C═NR¹⁰)NR¹⁰ ₂, —O—NR¹⁰ ₂, —O—NR¹⁰(C═W)R¹⁰, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SiR¹⁰ ₃, —SeR¹⁰, —PR¹⁰ ₂, —P(═W)R¹⁰ ₂, —SOR¹⁰, —SO₂R¹⁰, —PW₂R¹⁰ ₂, —PW₃R¹⁰ ₂, aryl and heterocyclyl,

of which the two mentioned last are optionally substituted by one or more radicals from the group

(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl, (C₆-C₈)-cycloalkynyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-haloalkynyl, halogen, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SiR¹⁰ ₃, —C(═W)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —SOR¹⁰, —SO₂R¹⁰, nitro, cyano and hydroxyl,

aryl,

which is optionally substituted by one or more radicals from the group

(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl and (C₆-C₈)-cycloalkynyl,

where these six abovementioned radicals are optionally substituted by one or more radicals from the group

halogen, cyano, nitro, —C(═W)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SOR¹⁰ and —SO₂R¹⁰;

halogen, cyano, nitro, —C(═W)R¹⁰, —C(═NOR¹⁰)R¹⁰, —C(═NNR¹⁰ ₂)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —OC(═W)R¹⁰, —OC(═W)OR¹⁰, —NR¹⁰C(═W)R¹⁰, —N[C(═W)R¹⁰]₂, —NR¹⁰C(═W)OR¹⁰, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SiR¹⁰ ₃, —PR¹⁰ ₂, —SOR¹⁰, —SO₂R¹⁰, —PW₂R¹⁰ ₂ and —PW₃R¹⁰ ₂;

pyridyl,

which is optionally substituted by one or more radicals from the group

(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl and (C₆-C₈)-cycloalkynyl,

where the six abovementioned radicals are optionally substituted by one or more radicals from the group

cyano, nitro, halogen, —C(═W)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SOR¹⁰ and —SO₂R¹⁰,

halogen, cyano, nitro, —C(═W)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —OC(═W)R¹⁰, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SOR¹⁰ and —SO₂R¹⁰;

—C(═W)R¹⁰, —C(═NOR¹⁰)R¹⁰, —C(═NNR¹⁰ ₂)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂ or halogen;

R⁴ and R⁵ together form a 4- to 7-membered ring which may be partially unsaturated and may be interrupted by one or more atoms from the group nitrogen, oxygen and sulfur, oxygen atoms not being directly adjacent to one another, and the ring optionally being substituted by one or more, but at most 5, radicals R¹;

R⁴ and R⁵ together form one of the groups ═O, ═S or ═N—R⁹;

R⁶ and R⁷ together form a 5- to 7-membered ring which may be partially unsaturated and may be interrupted by one or more atoms from the group nitrogen, oxygen and sulfur, oxygen atoms not being directly adjacent to one another, and the ring optionally being substituted by one or more, but at most 5, radicals R¹;

R⁶ and R⁷ together form one of the groups ═O, ═S or ═N—R⁹;

R⁸ is hydrogen,

(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkyl, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkyl, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkyl, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenyl, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenyl,

where the fourteen last-mentioned radicals are optionally substituted by one or more radicals from the group

halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy, (C₂-C₆)-alkynyloxy, (C₁-C₆)-haloalkyloxy, (C₂-C₆)-haloalkenyloxy, (C₂-C₆)-haloalkynyloxy, (C₃-C₈)-cycloalkoxy, (C₄-C₈)-cycloalkenyloxy, (C₃-C₈)-halocycloalkoxy, (C₄-C₈)-halocycloalkenyloxy, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkoxy, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkoxy, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenyloxy, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenyloxy, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkoxy, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkoxy, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkoxy, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenyloxy, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenyloxy, (C₁-C₄)-alkoxy-(C₁-C₆)-alkoxy, (C₁-C₄)-alkoxy-(C₂-C₆)-alkenyloxy, carbamoyl, (C₁-C₆)-mono- or dialkylcarbamoyl, (C₁-C₆)-mono- or dihaloalkylcarbamoyl, (C₃-C₈)-mono- or dicycloalkylcarbamoyl, (C₁-C₆)-alkoxycarbonyl, (C₃-C₈)-cycloalkoxycarbonyl, (C₁-C₆)-alkanoyloxy, (C₃-C₈)-cycloalkanoyloxy, (C₁-C₆)-haloalkoxycarbonyl, (C₁-C₆)-haloalkanoyloxy, (C₁-C₆)-alkaneamido, (C₁-C₆)-haloalkaneamido, (C₂-C₆)-alkeneamido, (C₃-C₈)-cycloalkaneamido, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkaneamido, (C₁-C₆)-alkylthio, (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio, (C₁-C₆)-haloalkylthio, (C₂-C₆)-haloalkenylthio, (C₂-C₆)-haloalkynylthio, (C₃-C₈)-cycloalkylthio, (C₄-C₈)-cycloalkenylthio, (C₃-C₈)-halocycloalkylthio, (C₄-C₈)-halocycloalkenylthio, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylthio, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylthio, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenylthio, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenylthio, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylthio, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylthio, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylthio, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylthio, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylthio, (C₁-C₆)-alkylsulfinyl, (C₂-C₆)-alkenylsulfinyl, (C₂-C₆)-alkynylsulfinyl, (C₁-C₆)-haloalkylsulfinyl, (C₂-C₆)-haloalkenylsulfinyl, (C₂-C₆)-haloalkynylsulfinyl, (C₃-C₈)-cycloalkylsulfinyl, (C₄-C₈)-cycloalkenylsulfinyl, (C₃-C₈)-halocycloalksulfinyl, (C₄-C₈)-halocycloalkenylsulfinyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylsulfinyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylsulfinyl, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenylsulfinyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenylsulfinyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylsulfinyl, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylsulfinyl, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylsulfinyl, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylsulfinyl, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylsulfinyl, (C₁-C₆)-alkylsulfonyl, (C₂-C₆)-alkenylsulfonyl, (C₂-C₆)-alkynylsulfonyl, (C₁-C₆)-haloalkylsulfonyl, (C₂-C₆)-haloalkenylsulfonyl, (C₂-C₆)-haloalkynylsulfonyl, (C₃-C₈)-cycloalkylsulfonyl, (C₄-C₈)-cycloalkenylsulfonyl, (C₃-C₈)-halocycloalkylsulfonyl, (C₄-C₈)-halocycloalkenylsulfonyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylsulfonyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylsulfonyl, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenylsulfonyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenylsulfonyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylsulfonyl, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylsulfonyl, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylsulfonyl, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylsulfonyl, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylsulfonyl, (C₁-C₆)-alkylamino, (C₂-C₆)-alkenylamino, (C₂-C₆)-alkynylamino, (C₁-C₆)-haloalkylamino, (C₂-C₆)-haloalkenylamino, (C₂-C₆)-haloalkynylamino, (C₃-C₈)-cycloalkylamino, (C₄-C₈)-cycloalkenylamino, (C₃-C₈)-halocycloalkamino, (C₄-C₈)-halocycloalkenylamino, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylamino, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylamino, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenylamino, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenylamino, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylamino, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylamino, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylamino, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylamino, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylamino, (C₁-C₆)-trialkylsilyl, aryl, aryloxy, arylthio, arylamino, arylcarbamoyl, aroyl, aroyloxy, aryloxycarbonyl, aryl-(C₁-C₄)-alkoxy, aryl-(C₂-C₄)-alkenyloxy, aryl-(C₁-C₄)-alkylthio, aryl-(C₂-C₄)-alkenylthio, aryl-(C₁-C₄)-alkylamino, aryl-(C₂-C₄)-alkenylamino, aryl-(C₁-C₆)-dialkylsilyl, diaryl-(C₁-C₆)-alkylsilyl, triarylsilyl and 5- or 6-membered heterocyclyl,

of which the nineteen last-mentioned radicals are optionally substituted in their cyclic moiety by one or more substituents from the group

halogen, cyano, nitro, amino, hydroxyl, thio, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-haloalkylthio, (C₁-C₄)-alkylamino, (C₁-C₄)-haloalkylamino, formyl and (C₁-C₄)-alkanoyl;

aryl, which is optionally substituted by one or more radicals from the group

halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy, (C₂-C₆)-alkynyloxy, (C₁-C₆)-haloalkyloxy, (C₂-C₆)-haloalkenyloxy, (C₂-C₆)-haloalkynyloxy, (C₃-C₈)-cycloalkoxy, (C₄-C₈)-cycloalkenyloxy, (C₃-C₈)-halocycloalkoxy, (C₄-C₈)-halocycloalkenyloxy, carbamoyl, (C₁-C₆)-mono- or dialkylcarbamoyl, (C₁-C₆)-alkoxycarbonyl, (C₁-C₆)-alkanoyloxy, (C₁-C₆)-mono- or dihaloalkylcarbamoyl, (C₁-C₆)-haloalkoxycarbonyl, (C₁-C₆)-haloalkanoyloxy, (C₁-C₆)-alkaneamido, (C₁-C₆)-haloalkaneamido, (C₂-C₆)-alkeneamido, (C₁-C₆)-alkylthio, (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio, (C₁-C₆)-haloalkylthio, (C₂-C₆)-haloalkenylthio, (C₂-C₆)-haloalkynylthio, (C₃-C₈)-cycloalkylthio, (C₄-C₈)-cycloalkenylthio, (C₃-C₈)-halocycloalkthio, (C₃-C₈)-halocycloalkenylthio, (C₁-C₆)-alkylsulfinyl, (C₂-C₆)-alkenylsulfinyl, (C₂-C₆)-alkynylsulfinyl, (C₁-C₆)-haloalkylsulfinyl, (C₂-C₆)-haloalkenylsulfinyl, (C₂-C₆)-haloalkynylsulfinyl, (C₃-C₈)-cycloalkylsulfinyl, (C₄-C₈)-cycloalkenylsulfinyl, (C₃-C₈)-halocycloalksulfinyl, (C₄-C₈)-halocycloalkenylsulfinyl, (C₁-C₆)-alkylsulfonyl, (C₂-C₆)-alkenylsulfonyl, (C₂-C₆)-alkynylsulfonyl, (C₁-C₆)-haloalkylsulfonyl, (C₂-C₆)-haloalkenylsulfonyl, (C₂-C₆)-haloalkynylsulfonyl, (C₃-C₈)-cycloalkylsulfonyl, (C₄-C₈)-cycloalkenylsulfonyl, (C₃-C₈)-halocycloalksulfonyl, (C₄-C₈)-halocycloalkenylsulfonyl, (C₁-C₆)-alkylamino, (C₂-C₆)-alkenylamino, (C₂-C₆)-alkynylamino, (C₁-C₆)-haloalkylamino, (C₂-C₆)-haloalkenylamino, (C₂-C₆)-haloalkynylamino, (C₃-C₈)-cycloalkylamino, (C₄-C₈)-cycloalkenylamino, (C₃-C₈)-halocycloalkamino and (C₄-C₈)-halocycloalkenylamino,

—C(═W)R¹¹, OR¹¹ or NR¹¹ ₂;

R⁹ is (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkyl, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenyl,

where the nine last-mentioned radicals are optionally substituted by one or more radicals from the group

halogen, cyano, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy, (C₂-C₆) alkynyloxy and (C₁-C₆)-haloalkyloxy;

R¹⁰ is hydrogen,

(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkyl, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkyl, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkyl, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenyl, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenyl,

where the fourteen last-mentioned radicals are optionally substituted by one or more radicals from the group

halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy, (C₂-C₆)-alkynyloxy, (C₁-C₆)-haloalkyloxy, (C₂-C₆)-haloalkenyloxy, (C₂-C₆)-haloalkynyloxy, (C₃-C₈)-cycloalkoxy, (C₄-C₈)-cycloalkenyloxy, (C₃-C₈)-halocycloalkoxy, (C₄-C₈)-halocycloalkenyloxy, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkoxy, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkoxy, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenyloxy, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenyloxy, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkoxy, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkoxy, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkoxy, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenyloxy, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenyloxy, (C₁-C₄)-alkoxy-(C₁-C₆)-alkoxy, (C₁-C₄)-alkoxy-(C₂-C₆)-alkenyloxy, carbamoyl,

(C₁-C₆)-mono- or dialkylcarbamoyl, (C₁-C₆)-mono- or dihaloalkylcarbamoyl, (C₃-C₈)-mono- or dicycloalkylcarbamoyl, (C₁-C₆)-alkoxycarbonyl, (C₃-C₈)-cycloalkoxycarbonyl, (C₁-C₆)-alkanoyloxy, (C₃-C₈)-cycloalkanoyloxy, (C₁-C₆)-haloalkoxycarbonyl, (C₁-C₆)-haloalkanoyloxy, (C₁-C₆)-alkaneamido, (C₁-C₆)-haloalkaneamido, (C₂-C₆)-alkeneamido, (C₃-C₈)-cycloalkaneamido, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkaneamido, (C₁-C₆)-alkylthio, (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio, (C₁-C₆)-haloalkylthio, (C₂-C₆)-haloalkenylthio, (C₂-C₆)-haloalkynylthio, (C₃-C₈)-cycloalkylthio, (C₄-C₈)-cycloalkenylthio, (C₃-C₈)-halocycloalkthio, (C₄-C₈)-halocycloalkenylthio, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylthio, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylthio, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenylthio, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenylthio, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylthio, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylthio, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylthio, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylthio, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylthio, (C₁-C₆)-alkylsulfinyl, (C₂-C₆)-alkenylsulfinyl, (C₂-C₆)-alkynylsulfinyl, (C₁-C₆)-haloalkylsulfinyl, (C₂-C₆)-haloalkenylsulfinyl, (C₂-C₆)-haloalkynylsulfinyl, (C₃-C₈)-cycloalkylsulfinyl, (C₄-C₈)-cycloalkenylsulfinyl, (C₃-C₈)-halocycloalksulfinyl, (C₄-C₈)-halocycloalkenylsulfinyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylsulfinyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylsulfinyl, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenylsulfinyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenylsulfinyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylsulfinyl, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylsulfinyl, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylsulfinyl, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylsulfinyl, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylsulfinyl, (C₁-C₆)-alkylsulfonyl, (C₂-C₆)-alkenylsulfonyl, (C₂-C₆)-alkynylsulfonyl, (C₁-C₆)-haloalkylsulfonyl, (C₂-C₆)-haloalkenylsulfonyl, (C₂-C₆)-haloalkynylsulfonyl, (C₃-C₈)-cycloalkylsulfonyl, (C₄-C₈)-cycloalkenylsulfonyl, (C₃-C₈)-halocycloalksulfonyl, (C₄-C₈)-halocycloalkenylsulfonyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylsulfonyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylsulfonyl, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenylsulfonyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenylsulfonyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylsulfonyl, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylsulfonyl, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylsulfonyl, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylsulfonyl, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylsulfonyl, (C₁-C₆)-alkylamino, (C₂-C₆)-alkenylamino, (C₂-C₆)-alkynylamino, (C₁-C₆)-haloalkylamino, (C₂-C₆)-haloalkenylamino, (C₂-C₆)-haloalkynylamino, (C₃-C₈)-cycloalkylamino, (C₄-C₈)-cycloalkenylamino, (C₃-C₈)-halocycloalkamino, (C₄-C₈)-halocycloalkenylamino, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylamino, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylamino, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenylamino, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenylamino, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylamino, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylamino, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylamino, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylamino, (C₁-C₆)-trialkylsilyl, aryl, aryloxy, arylthio, arylamino, aryl-(C₁-C₄)-alkoxy, aryl-(C₂-C₄)-alkenyloxy, aryl-(C₁-C₄)-alkylthio, aryl-(C₂-C₄)-alkenylthio, aryl-(C₁-C₄)-alkylamino, aryl-(C₂-C₄)-alkenylamino, aryl-(C₁-C₆)-dialkylsilyl, diaryl-(C₁-C₆)-alkylsilyl, triarylsilyl and 5- or 6-membered heterocyclyl,

where the cyclic moiety of the fourteen last-mentioned radicals is optionally substituted by one or more radicals from the group

halogen, cyano, nitro, amino, hydroxyl, thio, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₃-C₈)-cycloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-haloalkylthio, (C₁-C₄)-alkylamino, (C₁-C₄)-haloalkylamino, formyl and (C₁-C₄)-alkanoyl;

aryl, 5- or 6-membered heteroaromatic,

where the two last-mentioned radicals are optionally substituted by one or more radicals from the group

halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy, (C₂-C₆)-alkynyloxy, (C₁-C₆)-haloalkyloxy, (C₂-C₆)-haloalkenyloxy, (C₂-C₆)-haloalkynyloxy, (C₃-C₈)-cycloalkoxy, (C₄-C₈)-cycloalkenyloxy, (C₃-C₈)-halocycloalkoxy, (C₄-C₈)-halocycloalkenyloxy, carbamoyl, (C₁-C₆)-mono- or dialkylcarbamoyl, (C₁-C₆)-alkoxycarbonyl, (C₁-C₆)-alkanoyloxy, (C₁-C₆)-mono- or dihaloalkylcarbamoyl, (C₁-C₆)-haloalkoxycarbonyl, (C₁-C₆)-haloalkanoyloxy, (C₁-C₆)-alkaneamido, (C₁-C₆)-haloalkaneamido, (C₂-C₆)-alkeneamido, (C₁-C₆)-alkylthio, (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio, (C₁-C₆)-haloalkylthio, (C₂-C₆)-haloalkenylthio, (C₂-C₆)-haloalkynylthio, (C₃-C₈)-cycloalkylthio, (C₄-C₈)-cycloalkenylthio, (C₃-C₈)-halocycloalkthio, (C₄-C₈)-halocycloalkenylthio, (C₁-C₆)-alkylsulfinyl, (C₂-C₆)-alkenylsulfinyl, (C₂-C₆)-alkynylsulfinyl, (C₁-C₆)-haloalkylsulfnyl, (C₂-C₆)-haloalkenylsulfinyl, (C₂-C₆)-haloalkynylsulfinyl, (C₃-C₈)-cycloalkylsulfinyl, (C₄-C₈)-cycloalkenylsulfinyl, (C₃-C₈)-halocycloalksulfinyl, (C₄-C₈)-halocycloalkenylsulfinyl, (C₁-C₆)-alkylsulfonyl, (C₂-C₆)-alkenylsulfonyl, (C₂-C₆)-alkynylsulfonyl, (C₁-C₆)-haloalkylsulfonyl, (C₂-C₆)-haloalkenylsulfonyl, (C₂-C₆)-haloalkynylsulfonyl, (C₃-C₈)-cycloalkylsulfonyl, (C₄-C₈)-cycloalkenylsulfonyl, (C₃-C₈)-halocycloalksulfonyl, (C₄-C₈)-halocycloalkenylsulfonyl, (C₁-C₆)-alkylamino, (C₂-C₆)-alkenylamino, (C₂-C₆)-alkynylamino, (C₁-C₆)-haloalkylamino, (C₂-C₆)-haloalkenylamino, (C₂-C₆)-haloalkynylamino, (C₃-C₈)-cycloalkylamino, (C₄-C₈)-cycloalkenylamino, (C₃-C₈)-halocycloalkylamino and (C₄-C₈)-halocycloalkenylamino;

R¹¹ is (C₁-C₁₀)-alkyl, haloalkyl, aryl,

which is optionally substituted by one or more radicals from the group

halogen, cyano, nitro, (C₁-C₄)-alkoxy, (C₁-C₄)-alkyl, amino, (C₁-C₄)-monoalkylamino and (C₁-C₄)-dialkylamino;

NR¹⁰ ₂, OR¹⁰ or SR¹⁰.

The term “halogen” includes fluorine, chlorine, bromine and iodine.

The term “(C₁-C₄)-alkyl” is to be understood as a straight-chain or branched hydrocarbon radical having 1, 2, 3 or 4 carbon atoms, such as, for example, the methyl, ethyl, propyl, isopropyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl radical. Correspondingly, alkyl radicals having a greater range of carbon atoms are to be understood as straight-chain or branched saturated hydrocarbon radicals which contain a number of carbon atoms which corresponds to the range stated. Thus, the term “(C₁-C₆)-alkyl” includes the abovementioned alkyl radicals, and, for example, the pentyl, 2-methylbutyl, 1,1-dimethylpropyl, hexyl radical. The term “(C₁-C₁₀)-alkyl” is to be understood as the abovementioned alkyl radicals, and, for example, the nonyl, 1-decyl or 2-decyl radical and the term “(C₁-C₂₀)-alkyl” is to be understood as the abovementioned alkyl radicals, and, for example, the undecyl, dodecyl, pentadecyl or eicosyl radical.

“(C₁-C₄)-Haloalkyl” is to be understood as an alkyl group mentioned under the term “(C₁-C₄)-alkyl” in which one or more hydrogen atoms are replaced by the same number of identical or different halogen atoms, preferably by fluorine or chlorine, such as the trifluoromethyl, the 1-fluoroethyl, the 2,2,2-trifluoroethyl, the chloromethyl, fluoromethyl, the difluoromethyl and the 1,1,2,2-tetrafluoroethyl group.

“(C₁-C₄)-Alkoxy” is to be understood as an alkoxy group whose hydrocarbon radical has the meaning given under the term “(C₁-C₄)-alkyl”. Alkoxy groups embracing a greater range of carbon atoms are to be understood correspondingly.

The terms “alkenyl” and “alkynyl” having a prefix stating the range of carbon atoms denote a straight-chain or branched hydrocarbon radical having a number of carbon atoms corresponding to the range stated which comprises at least one multiple bond which may be in any position of the unsaturated radical in question. “(C₂-C₄)-Alkenyl” is thus, for example, the vinyl, allyl, 2-methyl-2-propene or 2-butenyl group; “(C₂-C₆)-alkenyl” denotes the abovementioned radicals and, for example, the pentenyl, 2-methylpentenyl or the hexenyl group. The term “(C₂-C₂₀)-alkenyl” is to be understood as the abovementioned radicals and, for example, the 2-decenyl or the 2-eicosenyl group. “(C₂-C₄)-Alkynyl” is, for example, the ethynyl, propargyl, 2-methyl-2-propyne or 2-butynyl group. “(C₂-C₆)-Alkynyl” is to be understood as the abovementioned radicals and, for example, the 2-pentynyl- or the 2-hexynyl group and “(C₂-C₂₀)-alkynyl” is to be understood as the abovementioned radicals and, for example, the 2-octynyl or the 2-decynyl group.

“(C₃-C₈)-Cycloalkyl” denotes monocyclic alkyl radicals, such as the cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl radical and bicyclic alkyl radicals, such as the norbornyl radical.

The term “(C₃-C₈)-cycloalkyl-(C₁-C₄)-alkyl” is to be understood as, for example, the cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclohexylethyl and cyclohexylbutyl radical, and the term “(C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl is to be understood as, for example, the 1-methylcyclopropyl, 1-methylcyclopentyl, 1-methylcyclohexyl, 3-hexylcyclobutyl and 4-tert-butyl-cyclohexyl radical.

“(C₁-C₄)-Alkoxy-(C₁-C₆)-alkyloxy” is an alkoxy group as defined above which is substituted by a further alkoxy group, such as, for example, 1-ethoxyethoxy.

“(C₃-C₈)-Cycloalkoxy” or “(C₃-C₈)-cycloalkylthio” is to be understood as one of the abovementioned (C₃-C₈)-cycloalkyl radicals which is linked via an oxygen or sulfur atom.

“(C₃-C₈)-Cycloalkyl-(C₁-C₆)-alkoxy” is, for example, the cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclohexylethoxy or the cyclohexylbutoxy group;

The term “(C₁-C₄)-alkyl-(C₃-C₈)-cycloalkoxy” is, for example, the methylcyclopropyloxy, methylcyclobutyloxy or the butylcyclohexyloxy group.

“(C₁-C₆)-Alkylthio” is an alkylthio group whose hydrocarbon radical has the meaning given under the term “(C₁-C₆)-alkyl”.

Correspondingly, “(C₁-C₆)-alkylsulfinyl” is, for example, the methyl-, ethyl-, propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl- or tert-butylsulfinyl group and “(C₁-C₆)-alkylsulfonyl” is, for example, the methyl-, ethyl-, propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl- or tert-butylsulfonyl group.

“(C₁-C₆)-Alkylamino” is a nitrogen atom which is substituted by one or two identical or different alkyl radicals of the above definition.

The term “(C₁-C₆)-mono- or dialkylcarbamoyl” is a carbamoyl group having one or two hydrocarbon radicals which have the meaning given under the term “(C₁-C₆-alkyl)” and which, in the case of two hydrocarbon radicals, may be identical or different.

Correspondingly, “(C₁-C₆)-dihaloalkylcarbamoyl” is a carbamoyl group which carries two (C₁-C₆)-haloalkyl radicals in accordance with the above definition or one (C₁-C₆)-haloalkyl radical and one (C₁-C₆)-alkyl radical in accordance with the above definition.

“(C₁-C₆)-Alkanoyl” is, for example, the acetyl, propionyl, butyryl or 2-methylbutyryl group.

The term “aryl” is to be understood as an isocyclic aromatic radical preferably having 6 to 14, in particular 6 to 12, carbon atoms, such as, for example, phenyl, naphthyl or biphenylyl, preferably phenyl. “Aroyl” is thus an aryl radical as defined above which is attached via a carbonyl group, such as, for example, the benzoyl group.

The term “heterocyclyl” denotes a cyclic radical which may be fully saturated, partially unsaturated or fully unsaturated and which may be interrupted by at least one or more identical atoms from the group nitrogen, sulfur or oxygen, oxygen atoms, however, not being directly adjacent to one another and at least one carbon atom being present in the ring, such as, for example, a thiophene, furan, pyrrole, thiazole, oxazole, imidazole, isothiazole, isoxazole, pyrazole, 1,3,4-oxadiazole, 1,3,4-thiadiazole, 1,3,4-triazole, 1,2,4-oxadiazole, 1,2,4-thiadiazole, 1,2,4-triazole, 1,2,3-triazole, 1,2,3,4-tetrazole, benzo[b]thiophene, benzo[b]furan, indole, benzo[c]thiophene, benzo[c]furan, isoindole, benzoxazole, benzothiazole, benzimidazole, benzisoxazole, benzisothiazole, benzopyrazole, benzothiadiazole, benzotriazole, dibenzofuran, dibenzothiophene, carbazole, pyridine, pyrazine, pyrimidine, pyridazine, 1,3,5-triazine, 1,2,4-triazine, 1,2,4,5-tetrazine, quinoline, isoquinoline, quinoxaline, quinazoline, cinnoline, 1,8-naphthyridine, 1,5-naphthyridine, 1,6-naphthyridine, 1,7-naphthyridine, phthalazine, pyridopyrimidine, purine, pteridine 4H-quinolizine; piperidine, pyrrolidine, oxazoline, tetrahydrofuran, tetrahydropyran, isoxazolidine or thiazolidine radical. The term “heteroaromatic” thus embraces, from among the meanings mentioned above under “heterocyclyl”, in each case the fully unsaturated aromatic heterocyclic compounds.

“Aryl-(C₁-C₄)-alkoxy” is an aryl radical which is attached via a (C₁-C₄)-alkoxy group, for example the benzyloxy, phenylethoxy, phenylbutoxy or naphthylmethoxy radical.

“Arylthio” is an aryl radical attached via a sulfur atom, for example the phenylthio or the 1- or 2-naphthylthio radical. Correspondingly, “aryloxy” is, for example, the phenoxy or 1- or 2-naphthyloxy radical.

“Aryl-(C₁-C₄)-alkylthio” is an aryl radical which is attached via an alkylthio radical, for example the benzylthio, naphthylmethylthio or the phenylethylthio radical.

The term “(C₁-C₆)-trialkylsilyl” denotes a silicon atom which carries three identical or different alkyl radicals in accordance with the above definition. Correspondingly “aryl-(C₁-C₆)-dialkylsilyl” is a silicon atom which carries one aryl radical and two identical or different radicals in accordance with the above definition, “diaryl-(C₁-C₆)-alkylsilyl” is a silicon atom which carries one alkyl radical and two identical or different aryl radicals in accordance with the above definition, and “triarylsilyl” is a silicon atom which carries three identical or different aryl radicals in accordance with the above definition.

In cases where two or more radicals R¹⁰ are present in a substituent, such as, for example, in —C(═W)NR¹⁰ ₂, these radicals may be identical or different.

Preference is given to those compounds of the formula I in which

Y is C₁-C₆-alkyl which is mono- or polysubstituted by chlorine and/or fluorine;

m is zero;

Q is a 5-membered heterocyclic group

 in which

a) X²=NR^(a) and X³=CR^(b)R¹ or

b) X²=CR^(a)R² and X³=CR^(b)R³ or

c) X²=CR⁴R⁵ and X³=CR⁶R⁷;

R^(a) and R^(b) together are a bond;

R¹, R², R³, R⁴ and R⁶ are each independently of one another hydrogen, halogen, C₁-C₁₂-alkyl, C₃-C₈-cycloalkyl, C₂-C₈-alkenyl, C₂-C₈-alkynyl, where the four last-mentioned hydrocarbon radicals are optionally mono- or polysubstituted by identical or different radicals from a group A1 consisting of C₁-C₆-alkylcarbonyl, C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylamino, C₁-C₆-alkylcarbonylamino, C₁-C₆-alkylsulfonylamino, phenyl, furyl, pyrryl, thienyl, halogen, cyano, phenyloxy, phenylthio and phenylamino, where the eleven first-mentioned radicals of group A1 are each optionally mono- or polysubstituted by identical or different radicals from a group B1 consisting of halogen, cyano, C₁-C₃-alkoxy and phenyl which is optionally mono- or polysubstituted by one or more halogen atoms and where the three last-mentioned radicals of group A1 are each optionally mono- or polysubstituted by identical or different radicals from a group B2 consisting of halogen, cyano, nitro, C₁-C₃-alkyl and C₁-C₃-alkoxy, or are C₁-C₆-alkylcarbonyl, C_(l)-C₆-alkylaminocarbonyl, C₁-C₆-alkoxycarbonyl, phenyl, pyridyl, furyl, thienyl, pyrryl, where the eight last-mentioned radicals are optionally mono- or polysubstituted by identical or different radicals from group B1, or are OR¹⁰, SR¹⁰ or N(R¹⁰)₂;

R⁵ and R⁷ are each independently of one another hydrogen, halogen, C₁-C₁₂-alkyl, C₃-C₈-cycloalkyl, C₂-C₈-alkenyl, C₂-C₈-alkynyl, where the four last-mentioned hydrocarbon radicals are optionally mono- or polysubstituted by identical or different radicals from a group A2 consisting of C₁-C₆-alkylcarbonyl, C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylamino, C₁-C₆-alkylcarbonylamino, phenyl, furyl, pyrryl, thienyl, halogen, cyano, phenyloxy, phenylthio and phenylamino, where the ten first-mentioned radicals of group A2 are each optionally mono- or polysubstituted by identical or different radicals from the group B1 and the three last-mentioned radicals of group A2 are each optionally mono- or polysubstituted by identical or different radicals from the group B2, or are C₁-C₆-alkylcarbonyl, C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkoxycarbonyl, phenyl, pyridyl, furyl, thienyl, pyrryl, where the eight last-mentioned radicals are optionally mono- or polysubstituted by identical or different radicals from the group B1, or are OR¹⁰, SR¹⁰ or N(R¹⁰)₂;

R¹⁰ is hydrogen, benzyl, C₁-C₆-alkyl, C₁-C₆-cycloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, phenyl, C₁-C₆-alkylcarbonyl or C₁-C₆-alkylsulfonyl, where the eight last-mentioned radicals are optionally mono- or polysubstituted by identical or different halogen atoms.

Particular preference is given to compounds of the formula I in which

Y is trifluoromethyl;

R¹, R², R³, R⁴ and R⁶ are each independently of one another halogen, C₁-C₁₂-alkyl, C₂-C₁₂-alkenyl, where the two last-mentioned radicals are optionally mono- or polysubstituted by identical or different radicals from a group A3 consisting of C₁-C₄-alkylcarbonyl, C₁-C₄-alkylaminocarbonyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylamino, C₁-C₄-alkylcarbonylamino, C₁-C₄-alkylsulfonylamino, phenyl, furyl, pyrryl, thienyl, fluorine, chlorine, bromine, cyano, phenyloxy, phenylthio and phenylamino, where the eleven first-mentioned radicals of group A3 are each optionally mono- or polysubstituted by identical or different radicals from the group B1 and the three last-mentioned radicals of group A3 are each optionally mono- or polysubstituted by identical or different radicals from the group B2, or are OR¹⁰, SR¹⁰ or N(R¹⁰)₂;

R⁵ and R⁷ are each independently of one another halogen, C₁-C₁₂-alkyl, C₂-C₁₂-alkenyl, where the two last-mentioned radicals are optionally mono- or polysubstituted by identical or different radicals from a group A4 consisting of C₁-C₄-alkylcarbonyl, C₁-C₄-alkylaminocarbonyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylamino, C₁-C₄-alkylcarbonylamino, phenyl, furyl, pyrryl, thienyl, fluorine, chlorine, bromine, cyano, phenyloxy, phenylthio and phenylamino, where the ten first-mentioned radicals of group A4 are each optionally mono- or polysubstituted by identical or different radicals from the group B1 and the three last-mentioned radicals of group A4 are each optionally mono- or polysubstituted by identical or different radicals from the group B2, or are OR¹⁰, SR¹⁰ or N(R¹⁰)₂;

R¹⁰ is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, phenyl, C₁-C₄-alkylcarbonyl or C₁-C₄-alkylsulfonyl, where the six last-mentioned radicals are optionally mono- or polysubstituted by identical or different halogen atoms.

Very particular preference is given to compounds of the formula I in which

R¹, R², R³, R⁴ and R⁶ are each independently of one another C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, where the two last-mentioned radicals are optionally mono- or polysubstituted by identical or different radicals from a group A5 consisting of C₁-C₄-alkylcarbonyl, C₁-C₄-alkylaminocarbonyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylamino, C₁-C₄-alkylcarbonylamino, C₁-C₄-alkylsulfonylamino, phenyl, fluorine, chlorine, bromine, cyano, phenyloxy, phenylthio and phenylamino, where the eight first-mentioned radicals of group A5 are each optionally mono- or polysubstituted by identical or different radicals from the group B1 and the three last-mentioned radicals of group A5 are each optionally mono- or polysubstituted by identical or different radicals from the group B2;

R⁵ and R⁷ are each independently of one another C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, where the two last-mentioned radicals are optionally mono- or polysubstituted by identical or different radicals from a group A6 consisting of C₁-C₄-alkylcarbonyl, C₁-C₄-alkylaminocarbonyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylamino, C₁-C₄-alkylcarbonylamino, phenyl, fluorine, chlorine, bromine, cyano, phenyloxy, phenylthio and phenylamino, where the seven first-mentioned radicals of group A6 are each optionally mono- or polysubstituted by identical or different radicals from the group B1 and the three last-mentioned radicals of group A6 are each optionally mono- or polysubstituted by identical or different radicals from the group B2.

Depending on the nature of the substituents defined above, the compounds of the formula (I) have acidic or basic properties and can form salts. If the compounds of the formula (I) carry, for example, groups such as hydroxyl, carboxyl and other groups inducing acidic properties, these compounds can be reacted with bases to give salts. Suitable bases are, for example, hydroxides, carbonates, bicarbonates of the alkali metals and alkaline earth metals, in particular those of sodium, potassium, magnesium and calcium, further ammonia, primary, secondary and tertiary amines having (C₁-C₄)-alkyl radicals and also mono-, di- and trialkanolamines of (C₁-C₄)-alkanols. If the compounds of the formula (I) carry, for example, groups such as amino, alkylamino and other groups inducing basic properties, these compounds can be reacted with acids to give salts. Suitable acids are, for example, mineral acids, such as hydrochloric acid, sulfuric acid and phosphoric acid, organic acids, such as acetic acid, oxalic acid and acidic salts, such as NaHSO₄ and KHSO₄. The salts which can be obtained in this manner likewise have insecticidal, acaricidal and nematicidal properties.

The compounds of the formula (I) may have one or more asymmetric carbon atoms or stereoisomers on double bonds. Enantiomers or diastereomers may therefore be present. The invention embraces both the pure isomers and mixtures thereof. The mixtures of diastereomers can be separated into the isomers by customary methods, for example by selective crystallization from suitable solvents or by chromatography. Racemates can be separated into the enantiomers by customary methods.

The present invention also provides processes for preparing compounds of the formula I:

To prepare compounds of the formula (I) in which

a) X¹=W, X²=NR^(a), X³=CR^(b)R¹

and R^(a), R^(b) and R¹ are as defined above and W is oxygen, activated derivatives of the acid of the formula (II)

where X and Y are as defined above, are reacted in the presence of a base with a compound of the formula (III)

in which the radical R¹ is as defined in formula (I). Suitable activated derivatives are, for example, acyl halides, esters and anhydrides. Suitable bases are amines, such as triethylamine, diisopropylethylamine, pyridine or lutidine, alkali metal hydroxides, alkali metal alkoxides, such as sodium ethoxide or potassium tert-butoxide, or alkylmetal compounds, such as butyllithium.

Depending on the conditions, the reaction described above can be carried out as a one-step process or as a two-step process via intermediates of the formula (IV):

Compounds of the formula (IV) can be cyclized to the 1,2,4-oxadiazoles by heating in an inert solvent at temperatures of up to 180° C.

Compounds of the formula (IV) are also directly obtainable from the acid of the formula (II) and amidoximes of the formula (III) by using a dehydrating reagent such as dicyclohexylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide or N,N′-carbonyldiimidazole.

Both acids of the formula (II) and amidoximes of the formula (III) are commercially available or can be prepared by methods known from the literature (see, for example: Houben-Weyl, Methoden der organischen Chemie, Volume X/4, pages 209-212; EP-A 0 580 374; G. F. Holland, J. N. Pereira, J. Med. Chem., 1967, 10, 149).

In the abovementioned case a) where W is sulfur, the compounds of the formula (I) can be obtained in a manner known from the literature by reaction of a compound of the formula (VII) with an electrophilic amination reagent, such as hydroxylamine-O-sulfonic acid (Y. Lin, S. A. Lang, S. R. Petty, J. Org. Chem. 1980, 45, 3750).

The compounds of the formula (VII) required as starting materials for this reaction can be prepared by reacting the thioamides of the formula (VIII) with dialkylamide dialkyl acetals, of formula (IX), where R¹ is as defined above and R¹² and R¹³ are each C₁-C₄-alkyl.

To prepare compounds of the formula (I) in which

b) X¹=NR^(a), X²=CR^(b)R¹, X³=W

and R^(a), R^(b) and R¹ are as defined above, and W is oxygen, amidoximes of the formula (V) can be reacted with activated derivatives of the acids of the formula (VI) or with the acids of the formula (VI) themselves.

To prepare compounds of the formula (I) in which

c) X¹=V, X²=CR^(a)R¹, X³=NR^(b)

and R^(a), R^(b) and R¹ are as defined above and V is sulfur, N,N′-diacylhydrazines of the formula (XIII) can be cyclized with a thiolation reagent, such as Lawesson's reagent (A. A. El-Barbary, S. Scheibyl, S. O. Lawesson, H. Fritz, Acta Chem. Scand. 1980, 597), in an inert solvent, such as toluene.

In the abovementioned case b) where W is oxygen, the compounds of the formula (I) can be prepared by reaction of acids of the formula (II) with hydrazines of the formula (X), in which R¹ is as defined above, using an activating reagent, such as phosphorus oxychloride or phosphorus pentachloride.

It is also possible to react acid hydrazides of the formula (XI) with ortho esters of the formula (XII) where R¹ is as defined above, and R¹² is (C₁-C₄)-alkyl.

The reaction can be carried out with or without solvent and with or without an activating reagent. Suitable solvents are hydrocarbons, such as toluene, or ethers, such as 1,2-dimethoxyethane. A suitable activating reagent is, for example, phosphorus oxychloride. The reaction temperature is generally the reflux temperature of the solvent.

To prepare compounds of the formula (I) in which

d) X¹=V, X²=CR^(a)R², X³=CR^(b)R³

and R^(a), R^(b) and R³ are as defined above and V is oxygen, compounds of the formula (XIV) are reacted with a dehydrating reagent.

Suitable dehydrating reagents are inorganic acyl chlorides, such as phosphorus oxychloride or thionyl chloride, inorganic acids, such as sulfuric acid or polyphosphoric acid, or a mixture of phosphoric acid and acetic anhydride (Houben-Weyl, Methoden der organischen Chemie, Volume E8a, pages 935-941).

The reaction can be carried out with or without a solvent. Suitable solvents are inert solvents, such as toluene, benzene, dimethoxyethane, dimethylformamide, dimethylacetamide and chlorobenzene. The reaction temperature is advantageously in a range between 50° C. and 150° C.

Compounds of the formula (XIV) can be obtained, for example, by oxidation of the corresponding hydroxyl compound of the formula (XV), it being possible to employ all reagents which are customarily used for this purpose in organic chemistry. (Milos Hudlický, “Oxidations in Organic Chemistry”, ACS Monograph 186, American Chemical Society, Washington, D.C., 1990)

In the abovementioned case d) where V is sulfur, the compounds of the formula (I) can be prepared by condensation of thioamides of the formula (XVII) with carbonyl derivatives of the formula (XVIII), where Z is halogen, in particular chlorine or bromine, acyloxy or sulfonyloxy, in particular methanesulfonyloxy or tolylsulfonyloxy.

To prepare compounds of the formula (I) in which

e) X¹=V, X²=CR⁴R⁵, X³=CR⁶R⁷

and R⁴, R⁵, R⁶ and R⁷ are as defined above and V is oxygen, compounds of the formula (XV) are reacted with cyclization reagents, such as Burgess' reagent (G. M. Atkins, E. M. Burgess, J. Am. Chem. Soc. 1968, 90, 4744.), in a solvent such as tetrahydrofuran and 1,4-dioxane, at a temperature which is in a range between room temperature and the reflux temperature of the solvent.

Compounds of the formula (XV) can be obtained by reacting activated derivatives of the acid in formula (II) with β-aminoalcohols of the formula (XVI), if appropriate in the presence of a base, such as, for example, triethylamine, in an inert solvent, such as, for example, dichlormethane.

An acyl halide or an anhydride can be used as activated derivative of the acid.

A number of β-aminoalcohols of the formula (XVI) are commercially available. For others, there is a large number of preparation procedures in the literature, for example a reduction of a-amino acids (B. M. Trost “Comprehensive Organic Synthesis, Reduction”, Volume 8, Pergamon Press, Oxford, 1991).

In the abovementioned case e) where V is sulfur, the compounds of the formula (I) can be prepared by reaction of thioamides of the formula (XVII) with compounds of the formula (XIX), the two substituents Z being as defined above and either identical or different (A. R. Katritzky “Comprehensive Heterocyclic Chemistry”, Volume 6, pages 306-312, Pergamon Press, Oxford).

Thioamides of the formula (XVII) are either commercially available or can be obtained by addition of hydrogen sulfide to the corresponding carbonitriles in the presence of a base (A. E. S. Fairfull, J. L. Lowe, D. A. Peak, J. Chem. Soc. 1952, 742).

For preparing compounds of the formula (I) in which

f) X¹=NR^(a), X²=CR^(b)R¹, X³=NR⁸

and R^(a), R^(b), R¹ and R⁸ are as defined above, hydrazides of the formula (XX)

are reacted with a compound of the formula (XXI) or with thioamides of the formula (XXII) (Houben-Weyl, Methoden der organischen Chemie, Volume E8d, pages 510-512).

This reaction can be carried out with or without using a solvent, suitable solvents being alcohols, such as ethanol and propanol, or aromatic hydrocarbons, such as toluene and xylene. If the reaction is carried out in a solvent, the reaction temperature to be chosen is advantageously the reflux temperature of the solvent. If, on the other hand, the reaction is carried out without a solvent, it is possible to heat up to 200° C., if appropriate.

Once the group Q has been assembled, for example by condensation, cyclization or cycloaddition reactions, the radicals R¹ to R⁹ may be derivatized further, if desired, employing the extensive arsenal of methods of organochemical synthesis.

To assemble compounds of the formula (I), in which m is 1, compounds of the formula (I) in which m is 0 can be treated with an oxidizing agent, such as, for example, meta-chloroperbenzoic acid.

The compounds of the formula (I) (also referred to as “active compounds” hereinbelow) have good plant tolerance, favorable homotherm toxicity and advantageous properties with respect to aquatic organisms and are suitable for controlling animal pests, in particular insects, arachnids (Acarina), helminths and mollusks, especially preferably for controlling insects and arachnids which are encountered in agriculture, in animal husbandry, in forests, in the preservation of stored products and materials and in the hygiene sector. They are active against normally sensitive and resistant species and all or individual stages of development. It has to be emphasized that the control of animal pests may be the result both of a toxic action of the compounds according to the invention and of a deterrant (repellant) action. The abovementioned pests include:

From the order of the Acarina, for example, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Eotetranychus spp., Oligonychus spp., and Eutetranychus spp.

From the order of the Isopoda, for example, Oniscus asselus, Armadium vulgar and Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus carpophagus and Scutigera spp.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Orthoptera, for example, Blatta orientalis, Periplaneta americana, Leucophaea madeirae, Blatella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis and Schistocerca gregaria.

From the order of the Isoptera, for example, Reticulitermes spp.

From the order of the Anoplura, for example, Phylloera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp. and Linognathus spp.

From the order of the Mallophaga, for example, Trichodectes spp. and Damalinea spp.

From the order of the Thysanoptera, for example, Hercinothrips femoralis, Thrips tabaci and Frankliniella spp.

From the order of the Heteroptera, for example, Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus and Triatoma spp.

From the order of the Homoptera, for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis spp., Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelus bilobatus, ephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. and Psylla spp.

From the order of the Lepidoptera, for example, Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Laphygma exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehnielia, Galleria mellonella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana, Cuaphalocrocis spp. and Manduca spp.

From the order of the Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylloides chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonumus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrynchus assimilis, Hypera postica, Dermestes spp., Trogoderma, Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica and Lissorhoptus spp.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hypobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae and Tipula paludosa.

From the order of the Siphonaptera, for example, Xenopsylla cheopsis and Ceratophyllus spp. From the order of the Arachnida, for example, Scorpio maurus and Latrodectus mactans. From the class of helminths, for example, Haemonchus, Trichostrongulus, Ostertagia, Cooperia, Chabertia, Strongyloides, Oesophagostomum, Hyostrongulus, Ancylostoma, Ascaris and Heterakis, as well as Fasciola. From the class of Gastropoda, for example, Deroceras spp., Arion spp., Lymnaea spp., Galba spp., Succinea spp., Biomphalaria spp., Bulinus spp. and Oncomelania spp. From the class of Bivalva, for example, Dreissena spp.

The phytoparasitic nematodes which can be controlled according to the invention include, for example, the root-parasitic soil nematodes, such as, for example, those of the genera Meloidogyne (root gall nematodes, such as Meloidogyne incognita, Meloidogyne hapla and Meloidogyne javanica), Heterodera and Globodera (cyst-forming nematodes, such as Globodera rostochiensis, Globodera pallida and Heterodera trifolii) and of the genera Radopholus (such as Radopholus similis), Pratylenchus (such as Pratylenchus neglectus, Pratylenchus penetrans and Pratylenchus curvitatus), Tylenchulus (such as Tylenchulus semipenetrans), Tylenchorhynchus (such as Tylenchorhynchus dubius and Tylenchorhynchus claytoni), Rotylenchus (such as Rotylencus robustus), Heliocotylenchus (such as Heliocotylenchus multicinctus), Belonoaimus (such as Belonoaimus longicaudatus), Longidorus (such as Longidorus elongatus), Trichodorus (such as Trichodorus primitivus) and Xiphinema (such as Xiphinema index).

The nematode genera Ditylenchus (stem parasites, such as Ditylenchus dipsaci and Ditylenchus destructor), Aphelenchoides (leaf nematodes, such as Aphelenchoides ritzemabosi) and Anguina (blossom nematodes, such as Anguina tritici) can furthermore be controlled with the compounds according to the invention.

The invention also relates to compositions, in particular insecticidal and acaricidal compositions, which comprise the compounds of the formula (I) in addition to suitable formulation auxiliaries.

The compositions according to the invention in general comprise the active compounds of the formula (I) to the extent of 1 to 95% by weight. They can be formulated in various ways, depending on how this is determined by the biological and/or chemico-physical parameters. Suitable formulation possibilities are therefore: Wettable powders (WP), emulsifiable concentrates (EC), aqueous solutions (SL), emulsions, sprayable solutions, oil- or water-based dispersions, suspension concentrates (SC), suspoemulsions (SE), dusting powders (DP), seed dressings, granules in the form of microgranules, sprayed granules, absorption granules and adsorption granules, water-dispersible granules (WG), ULV formulations, microcapsules, waxes or baits.

These individual types of formulation are known in principle and are described, for example, in: Winnacker-Küchler, “Chemische Technologie” [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th Edition 1986; van Falkenberg, “Pesticides Formulations”, Marcel Dekker N.Y., 2nd Edition 1972-73; K. Martens, “Spray Drying Handbook”, 3rd Edition 1979, G. Goodwin Ltd. London.

The necessary formulation auxiliaries, i.e. carrier substances and surface-acting substances, such as inert materials, surfactants, solvents and further additives, are likewise known and are described, for example, in: Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2nd Edition, Darland Books, Caldwell N.J.; H. v. Olphen, “Introduction to Clay Colloid Chemistry”, 2nd Edition, J. Wiley & Sons, N.Y.; Marsden, “Solvents Guide”, 2nd Edition, Interscience, N.Y. 1950; McCutcheon's, “Detergents and Emulsifiers Annual”, MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface Active Agents”, Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, “Grenzflächenaktive Äthylenoxidaddukte” [Surface-active ethylene oxide adducts], Wiss. Verlagsgesell., Stuttgart 1967; Winnacker-Küchler, “Chemische Technologie” [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th Edition 1986.

Combinations with other substances having a pesticidal action, fertilizers and/or growth regulators can be prepared on the basis of these formulations, for example in the form of a ready-to-use formulation or as a tank mix. Wettable powders are preparations which are uniformly dispersible in water and which, alongside the active compound, and in addition to a diluent or inert substance, also comprise wetting agents, for example polyethoxylated alkylphenols, polyethoxylated fatty alcohols or alkyl- or alkylphenol-sulfonates, and dispersing agents, for example sodium ligninsulfonate or sodium 2,2′-dinaphthylmethane-6,6′-disulfonate. Emulsifiable concentrates are prepared by dissolving the active compound in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or also higher-boiling aromatics or hydrocarbons, with the addition of one or more emulsifiers. Emulsifiers which can be used are, for example: calcium alkylarylsulfonates, such as Ca dodecylbenzenesulfonate, or nonionic emulsifiers, such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide condensation products, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylene sorbitol esters.

Dusting powders are obtained by grinding the active compound with finely divided solid substances, for example talc, naturally occurring clays, such as kaolin, bentonite and pyrophillite, or diatomaceous earth. Granules can be prepared either by spraying the active compound onto granular inert material capable of adsorption or by applying active compound concentrates to the surface of carrier substances, such as sand, kaolinites or granular inert material, by means of adhesives, for example polyvinyl alcohol, sodium polyacrylate or mineral oils. Suitable active compounds can also be granulated in the manner customary for the preparation of fertilizer granules—if desired as a mixture with fertilizers.

In wettable powders, the active compound concentration is generally about 10 to 90% by weight, the remainder to make up 100% by weight comprising customary formulation constituents. In emulsifiable concentrates, the active compound concentration can be about 5 to 80% by weight. Dust-like formulations usually comprise 5 to 20% by weight of active compound, and sprayable solutions about 2 to 20% by weight. In granules, the content of active compound partly depends on whether the active compound is present in liquid or solid form and what granulating auxiliaries, fillers and the like are used.

In addition, the active compound formulations mentioned comprise, if appropriate, the particular customary tackifiers, wetting agents, dispersing agents, emulsifiers, penetration agents, solvents, fillers or carriers.

For use, the concentrates in the commercially available form are diluted in the customary manner, if appropriate, for example by means of water in the case of wettable powders, emulsifiable concentrates, dispersions and in some cases also microgranules. Dust-like and granular formulations as well as sprayable solutions are usually not diluted further with additional inert substances before use.

The required amount applied varies with external conditions, such as temperature, humidity and the like. It can vary within wide limits, for example between 0.0005 and 10.0 kg/ha or more of active substance, but is preferably between 0.001 and 5 kg/ha.

The active compounds according to the invention can be present in their commercially available formulations and in the use forms prepared from these formulations as mixtures with other active compounds, such as insecticides, attractants, sterilizing agents, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.

The pest control agents include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, formamidines, tin compounds, substances produced by microorganisms and the like.

Preferred partners for the mixtures are

1. from the group of phosphorus compounds

acephate, azamethiphos, azinphos-ethyl-, azinphosmethyl, bromophos, bromophos-ethyl, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, demeton, demeton-S-methyl, demeton-S-methyl sulfone, dialifos, diazinon, dichlorvos, dicrotophos, O,O-1,2,2,2-tetrachloroethyl phosphorthioate (SD 208 304), dimethoate, disulfoton, EPN, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitriothion, fensulfothion, fenthion, fonofos, formothion, heptenophos, isozophos, isothioate, isoxathion, malathion, methacrifos, methamidophos, methidathion, salithion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosfolan, phosmet, phosphamidon, phoxim, pirimiphos, primiphos-ethyl, pirimiphos-methyl, profenofos, propaphos, proetamphos, prothiofos, pyraclofos, pyridapenthion, quinalphos, sulprofos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorphon, vamidothion;

2. from the group of carbamates

aldicarb, 2-sec-butylphenyl methylcarbamate (BPMC), carbaryl, carbofuran, carbosulfan, cloethocarb, benfuracarb, ethiofencarb, furathiocarb, isoprocarb, methomyl, 5-methyl-m-cumenyl butyryl(methyl)carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, ethyl 4,6,9-triaza-4-benzyl-6,10-dimethyl-8-oxa-7-oxo-5,11-dithia-9-dodecenoate (OK 135), 1-methylthio(ethylideneamino) N-methyl-N-(morpholinothio)carbamate (UC 51717);

3. from the group of carboxylic acid esters

allethrin, alphametrin, 5-benzyl-3-furylmethyl (E)-(1R)-cis, 2,2-di-methyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate, bioallethrin, bioallethrin ((S)-cyclopentyl isomer), bioresmethrin, biphenate, (RS)-1-cyano-1-(6-phenoxy-2-pyridyl)methyl (1RS)-trans-3-(4-tert-butylphenyl)-2,2-dimethylcyclopropanecarboxylate (NCI 85193), cycloprothrin, cyhalothrin, cythithrin, cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, fenfluthrin, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (D isomer), permethrin, pheothrin ((R) isomer), d-pralethrin, pyrethrins (naturally occurring products), resmethrin, tefluthrin, tetramethrin and tralomethrin;

4. from the group of amidines

amitraz, chlordimeform;

5. from the group of tin compounds

cyhexatin, fenbutatin oxide;

6. others

abamectin, Bacillus thuringiensis, bensultap, binapacryl, bromopropylate, buprofezin, camphechlor, cartap, chlorobenzilate, chlorfluazuron, 2-(4-chlorophenyl)-4,5-diphenylthiophene (UBI-T 930), chlorfentezine, 2-naphthylmethyl cyclopropanecarboxylate (Ro 12-0470), cyromazin, N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propyloxy)phenyl)carbamoyl)-2-chlorobenzocarboximide acid ethyl ester, dicofol, N-(N-(3,5-di-chloro-4-(1,1,2,2-tetrafluoroethoxy)phenylamino)carbonyl)-2,6-difluorobenzamide (XRD 473), diflubenzuron, N-(2,3-dihydro-3-methyl-1,3-thiazol-2-ylidene)-2,4-xylidene, dinobuton, dinocap, endosulfan, ethofenprox, (4-ethoxyphenyl)(dimethyl)(3-(3-phenoxyphenyl)propyl)silane, (4-ethoxyphenyl)(3-(4-fluoro-3-phenoxyphenyl)propyl)dimethylsilane, fenoxycarb, 2-fluoro-5-(4-(4-ethoxyphenyl)-4-methyl-1-pentyl)diphenyl ether (MTI 800), granulosis and nuclear polyhedrosis viruses, fenthiocarb, flubenzimine, flucycloxuron, flufenoxuron, gamma-HCH, hexythiazox, hydramethylnon (AC 217300), ivermectin, 2-nitromethyl-4,5-dihydro-6H-thiazine (DS 52618), 2-nitromethyl-3,4-dihydrothiazole (SD 35651), 2-nitromethylene-1,2-thiazinan-3-ylcarbamaldehyde (WL 108477), propargite, teflubenzuron, tetradifon, tetrasul, thiocyclam, trifumuron, imidacloprid.

The abovementioned combination partners are known active compounds, and most of them are described in Ch. R. Worthing, S. B. Walker, The Pesticide Manual, 7th Edition (1983), British Crop Protection Council.

The active compound content of the use forms prepared from the commercially available formulations can be from 0.00000001 to 95% by weight of active compound, preferably between 0.00001 and 1% by weight.

The active compounds are used in a customary manner appropriate for the use forms.

The active compounds according to the invention are also suitable for controlling endo- and ectoparasites in the veterinary medicine field and in the field of animal husbandry. The active compounds according to the invention are used here in a known manner, such as by oral use in the form of, for example, tablets, capsules, potions or granules, by means of dermal use in the form of, for example, dipping, spraying, pouring-on, spotting-on and dusting, and by parenteral use in the form of, for example, injection.

The novel compounds of the formula (I) can accordingly also particularly advantageously be used in livestock husbandry (for example cattle, sheep, pigs and poultry, such as chickens, geese and the like). In a preferred embodiment of the invention, the compounds are administered orally to the animals, if appropriate in suitable formulations (cf. above) and if appropriate with the drinking water or feed. Since excretion in the faeces takes place in an active manner, the development of insects in the faeces of the animals can be prevented very easily in this way. The dosages and formulations suitable in each case depend in particular on the species and the development stage of the stock animals and also on the pressure of infestation, and can easily be determined and specified by the customary methods. The novel compounds can be employed in cattle, for example, in dosages of 0.01 to 1 mg/kg of body weight.

In addition to the application methods mentioned hereinabove, the active compounds of the formula I according to the invention also have excellent systemic action. The active compounds can therefore also be introduced into the plants via below-ground and above-ground parts of plants (root, stem, leaf), when the active compounds are applied in liquid or solid form to the immediate surroundings of the plants (for example granules in soil application, application in flooded rice fields).

Furthermore, the active compounds according to the invention are particularly useful for treating vegetative and generatative propagation stock, such as, for example, seed of, for example, cereals, vegetables, cotton, rice, sugar beet and other crops and ornamentals, of bulbs, cuttings and tubers of other vegetatively propagated crops and ornamentals. To this end, treatment can be carried out prior to sowing or planting (for example by special seed coating techniques, by seed dressings in liquid or solid form or by seed box treatment), during sowing or planting or after sowing or planting by special application techniques (for example seed row treatment). Depending on the application, the amount of active compound applied can vary within a relatively wide range. In general, the application rates are between 1 g and 10 kg of active compound per hectare of soil area.

In a preferred embodiment, the invention provides 4-trifluoromethyl-3-oxadiazolyl, pyridine derivatives of the formula (I′),

where the symbols and indices are as defined below:

m is 0 or 1;

X is a single bond, a straight-chain alkylene group having 1, 2 or 3 carbon atoms or a branched alkylene group having 3 to 9 carbon atoms, where one or more H atoms may be replaced by F;

Y is —O—, —S—, —SO—, —SO₂—, —O—CO—, —O—CO—O—, —SO₂—O—, —O—SO₂—, —NR¹—, —NR²—CO—, —NR³—CO—O—, —NR⁴—CO—NR⁵—, —O—CO—CO—O—, —O—CO—NR⁶, —SO₂—NR⁷ or —NR⁸—SO₂—;

R, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸ are identical or different and are independently of one another H, (C₁-C₁₀)-alkyl, (C₂-C₁₀)-alkenyl, (C₂-C₁₀)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl, (C₆-C₈)-cycloalkynyl, heterocyclyl or —(CH₂)₁₋₄-heterocyclyl, where each of the eight last-mentioned groups is unsubstituted or mono- or polysubstituted, and where, optionally R and R¹, R and R², R and R⁵, R and R⁶, R and R⁷, R and R⁸ or X and R together form a ring system,

with the proviso, that the compounds in which

X=-, Y=O, R=H

X=-, Y=O, R=Me

X=-, Y=O, R=Et

X=-, Y=O, R=CHF₂

X=-, Y=O, R=CH₂Ph

X=CH₂, Y=O, R=2-furanyl

X=CH₂, Y=O, R=Me

X=CH₂, Y=O, R=5-isoxazolyl

X=CH₂, Y=O, R=5-nitrofuran-2-yl

X=CH₂CH₂, Y=O, R=H

X=CH₂CH₂; Y=O, R=Me

X=CH₂CH₂, Y=O,

X=CH₂CH₂, Y=O, R=Et

X=CH₂CH₂, Y=O, R=H

X=CH₂CH₂; Y=OC(O), R=4-F-phenyl

X=CH₂CH₂, Y=OC(O), R=2,6-difluorophenyl

X=CH₂CH₂, Y=OC(O), R=4-nitrophenyl

X=CH₂CH₂, Y=OC(O), R=t-Bu

X=CH₂CH₂, Y=OC(O), R=cyclopropyl

X=CH₂CH₂, Y=OC(O), R=Me

X=CH₂CH₂CH₂, Y=O, R=H

X=-, Y=S(O), R=4-bromobenzyl

X=CH₂, Y=S, R=Me

X=CH₂, Y=S(O), R=Me

X=CH₂, Y=S(O)₂, R=t-Bu

X=CH₂, Y=S, R=2-thienyl

X=CH₂CH₂, Y=S, R=Me

X=CH₂CH₂, Y=S, R=n-Pr

X=CH₂CH₂, Y=S, R=benzyl

X=CH₂CH₂, Y=S, R=2-thienylmethyl

X=CH₂CH₂CH₂, Y=S, R=Me

X=CH₂CH₂CH₂, Y=S(O), R=Me

X=CH₂CH₂CH₂CH₂, Y=S, R=CH₂CH₂CH₂CH₂OMe

are not included.

m is preferably 0.

If m is 1 and Y contains an S(O)_(n) group, n is preferably 2.

X is preferably a single bond, CH₂, CH₂—CH₂, CH₂—CH(CH₃) or —CH₂—C(CH₃)₂—.

Y is preferably —O—, —S—, —SO—, —SO₂—, —O—CO—, —O—CO—O, —O—CO—NR⁶—, —SO—NR⁷—, —O—Sμ₂— or —SO₂—O—.

R, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸ are preferably identical or different and are independently of one another H, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl, (C₆-C₈)-cycloalkynyl, heterocyclyl or —(CH₂)₁₋₄-heterocyclyl,

where the eight last-mentioned radicals are unsubstituted or substituted by one or more radicals from the group consisting of

halogen, cyano, citro, hydroxyl, —C(═W)R⁹, (═W), —C(═NOR⁹)R⁹, —C(═NNR⁹ ₂)R⁹, —C(═W)OR⁹, —C(═W)NR⁹ ₂, —OC(═W)R⁹, —OC(═W)OR⁹, —NR⁹C(═W)R⁹, —N[C(═W)R⁹]₂, —NR⁹C(═W)OR⁹, —C(═W)NR⁹—NR⁹ ₂, —C(═W)NR⁹—NR⁹[C(═W)R⁹], —NR⁹—C(═W)NR⁹ ₂, —NR⁹—NR⁹C(═W)R⁹, —NR⁹—N[C(═W)R⁹]₂, —N[(C═W)R⁹]—NR⁹ ₂, —NR⁹—N[(C═W)R⁹]₂, —NR⁹—NR⁹[(C═W)WR⁹], —NR⁹—[(C═W)NR⁹2], —NR⁹(C═NR⁹)R⁹, —NR⁹(C═NR⁹)NR⁹ ₂, —O—NR⁹ ₂, —O—NR⁹(C═W)R⁹, —SO₂NR⁹ ₂, —NR⁹SO₂R⁹, —SO₂OR⁹, —OSO₂R⁹, —OR⁹, —NR⁹ ₂, —SR⁹, —SiR⁹ ₃, —SeR⁹, —PR⁹ ₂, —P(═W)R⁹ ₂, —SOR⁹, —SO₂R⁹, —PW₂R⁹ ₂, —PW₃R⁹ ₂, aryl and heterocyclyl,

the two last-mentioned radicals of which are unsubstituted or substituted by one or more radicals from the group consisting of

(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl, (C₆-C₈)-cycloalkynyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-haloalkynyl, halogen, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SiR¹⁰ ₃, —C(═W)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —SOR¹⁰, —SO₂R¹⁰, nitro, cyano and hydroxyl,

and where optionally R and R¹, R and R⁵, R and R⁶, R and R⁷ and R and R⁸ together are —(CH₂)₄—, —(CH₂)₅—, —(CH₂)₂—O—(CH₂)₂—, (CH₂)₂—NR²—(CH₂)₂—

and where X and R together, if appropriate, may also form a ring system,

and where optionally R and R¹, R and R², R and R⁵, R and R⁶, R and R⁷, R and R⁸ or X and R together form a ring system.

Preferred to form the ring system are —(CH₂)₃—, —(CH₂)₄—, —(CH₂)₅—, —(CH₂)₂—O—(CH₂)₂—, —(CH₂)₂—NR³—(CH₂)₂—, -(thiophen-3,4-diyl)—C(O)—, CH(imidazolyl-)CF₂C(O)—, —CH(Me)CH₂C(O)—, —CMe₂CH₂C(O)—, —CH(Me)CH(Me)C(O)—, —CH₂CH₂CH₂C(O)—, —CH(Me)CH₂CH₂C(O)—, —CH₂CH(Me)CH₂C(O)—, —CH₂CMe₂CH₂C(O)—, —CH₂C[—(CH₂)₄—]CH₂C(O)—, -(1,2-cyclohexylene)-C(O)—, -(cyclohexene-4,5-diyl)-C(O)—, —CH₂—C(H)Ph—CH₂—C(O)—, —CMe═CMe—C(O)—, —CH₂—CH₂—C(O)—, especially preferred are —(CH₂)₃—, —(CH₂)₄—, —(CH₂)₅—, —(CH₂)₂—O—(CH₂)₂—, —(CH₂)₂—NR³—(CH₂)₂—.

W is O or S.

R⁹ is hydrogen,

(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkyl, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkyl, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkyl, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenyl, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenyl,

where the fourteen last-mentioned radicals are unsubstituted or substituted by one or more radicals from the group consisting of

halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy, (C₂-C₆)-alkynyloxy, (C₁-C₆)-haloalkyloxy, (C₂-C₆)-haloalkenyloxy, (C₂-C₆)-haloalkynyloxy, (C₃-C₈)-cycloalkoxy, (C₄-C₈)-cycloalkenyloxy, (C₃-C₈)-halocycloalkoxy, (C₄-C₈)-halocycloalkenyloxy, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkoxy, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkoxy, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenyloxy, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenyloxy, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkoxy, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkoxy, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkoxy, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenyloxy, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenyloxy, (C₁-C₄)-alkoxy-(C₁-C₆)-alkoxy, (C₁-C₄)-alkoxy-(C₂-C₆)-alkenyloxy, carbamoyl, (C₁-C₆)-mono- or -dialkylcarbamoyl, (C₁-C₆)-mono- or dihaloalkylcarbamoyl, (C₃-C₈)-mono- or dicycloalkylcarbamoyl, (C₁-C₆)-alkoxycarbonyl, (C₃-C₈)-cycloalkoxycarbonyl, (C₁-C₆)-alkanoyloxy, (C₃-C₈)-cycloalkanoyloxy, (C₁-C₆)-haloalkoxycarbonyl, (C₁-C₆)-haloalkanoyloxy, (C₁-C₆)-alkanamido, (C₁-C₆)-haloalkanamido, (C₂-C₆)-alkenamido, (C₃-C₈)-cycloalkanamido, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkanamido, (C₁-C₆)-alkylthio, (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio, (C₁-C₆)-haloalkylthio, (C₂-C₆)-haloalkenylthio, (C₂-C₆)-haloalkynylthio, (C₃-C₈)-cycloalkylthio, (C₄-C₈)-cycloalkenylthio, (C₃-C₈)-halocycloalkylthio, (C₄-C₈)-halocycloalkenyllthio, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylthio, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylthio, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenylthio, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenylthio, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylthio, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylthio, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylthio, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylthio, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylthio, (C₁-C₆)-alkylsulfinyl, (C₂-C₆)-alkenylsulfinyl, (C₂-C₆)-alkynylsulfinyl, (C₁-C₆)-haloalkylsulfinyl, (C₂-C₆)-haloalkenylsulfinyl, (C₂-C₆)-haloalkynylsulfinyl, (C₃-C₈)-cycloalkylsulfinyl, (C₄-C₈)-cycloalkenylsulfinyl, (C₃-C₈)-halocycloalkylsulfinyl, (C₄-C₈)-halocycloalkenylsulfinyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylsulfinyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylsulfinyl, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenylsulfinyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenylsulfinyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylsulfinyl, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylsulfinyl, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylsulfinyl, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylsulfinyl, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylsulfinyl, (C₁-C₆)-alkylsulfonyl, (C₂-C₆)-alkenylsulfonyl, (C₂-C₆)-alkynylsulfonyl, (C₁-C₆)-haloalkylsulfonyl, (C₂-C₆)-haloalkenylsulfonyl, (C₂-C₆)-haloalkynylsulfonyl, (C₃-C₈)-cycloalkylsulfonyl, (C₄-C₈)-cycloalkenylsulfonyl, (C₃-C₈)-halocycloalkylsulfonyl, (C₄-C₈)-halocycloalkenylsulfonyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylsulfonyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylsulfonyl, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenylsulfonyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenylsulfonyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylsulfonyl, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylsulfonyl, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylsulfonyl, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylsulfonyl, (C₁-C₆)-alkylamino, (C₂-C₆)-alkenylamino, (C₂-C₆)-alkynylamino, (C₁-C₆)-haloalkylamino, (C₂-C₆)-haloalkenylamino, (C₂-C₆)-haloalkynylamino, (C₃-C₈)-cycloalkylamino, (C₄-C₈)-cycloalkenylamino, (C₃-C₈)-halocycloalkylamino, (C₄-C₈)-halocycloalkenylamino, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylamino, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylamino, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenylamino, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenylamino, (C₁-C₆)-alkyllkylamino, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylamino, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylamino, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylamino, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylamino, (C₁-C₆)-trialkylsilyl, aryl, aryloxy, arylthio, arylamino, aryl-(C₁-C₄)-alkoxy, aryl-(C₂-C₄)-alkenyloxy, aryl-(C₁-C₄)-alkylthio, aryl-(C₂-C₄)-alkenylthio, aryl-(C₁-C₄)-alkylamino, aryl-(C₂-C₄)-alkenylamino, aryl-(C₁-C₆)-dialkylsilyl, diaryl-(C₁-C₆)-alkylsilyl, triarylsilyl and 5- or 6-membered heterocyclyl,

where the cyclic moiety of the fourteen last-mentioned radicals is unsubstituted or substituted by one or more radicals from the group consisting of

halogen, cyano, nitro, amino, hydroxyl, thio, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₃-C₈)-cycloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-haloalkylthio, (C₁-C₄)-alkylamino, (C₁-C₄)-haloalkylamino, formyl and (C₁-C₄)-alkanoyl,

aryl, 4-, 5- or 6-membered heterocyclyl,

where the two last-mentioned radicals are unsubstituted or substituted by one or more radicals from the group consisting of

halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy, (C₂-C₆)-alkynyloxy, (C₁-C₆)-haloalkyloxy, (C₂-C₆)-haloalkenyloxy, (C₂-C₆)-haloalkynyloxy, (C₃-C₈)-cycloalkoxy, (C₄-C₈)-cycloalkenyloxy, (C₃-C₈)-halocycloalkoxy, (C₄-C₈)-halocycloalkenyloxy, carbamoyl, (C₁-C₆)-mono- or -dialkylcarbamoyl, (C₁-C₆)-alkoxycarbonyl, (C₁-C₆)-alkanoyloxy, (C₁-C₆)-mono- or -dihaloalkylcarbamoyl, (C₁-C₆)-haloalkoxycarbonyl, (C₁-C₆)-haloalkanoyloxy, (C₁-C₆)-alkanamido, (C₁-C₆)-haloalkanamido, (C₂-C₆)-alkenamido, (C₁-C₆)-alkylthio, (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio, (C₁-C₆)-haloalkylthio, (C₂-C₆)-haloalkenylthio, (C₂-C₆)-haloalkynylthio, (C₃-C₈)-cycloalkylthio, (C₄-C₈)-cycloalkenylthio, (C₃-C₈)-halocycloalkylthio, (C₄-C₈)-halocycloalkenylthio, (C₁-C₆)-alkylsulfinyl, (C₂-C₆)-alkenylsulfinyl, (C₂-C₆)-alkynylsulfinyl, (C₁-C₆)-haloalkylsulfinyl, (C₂-C₆)-haloalkenylsulfinyl, (C₂-C₆)-haloalkynylsulfinyl, (C₃-C₈)-cycloalkylsulfinyl, (C₄-C₈)-cycloalkenylsulfinyl, (C₃-C₈)-halocycloalkylsulfinyl, (C₄-C₈)-halocycloalkenylsulfinyl, (C₁-C₆)-alkylsulfonyl, (C₂-C₆)-alkenylsulfonyl, (C₂-C₆)-alkynylsulfonyl, (C₁-C₆)-haloalkylsulfonyl, (C₂-C₆)-haloalkenylsulfonyl, (C₂-C₆)-haloalkynylsulfonyl, (C₃-C₈)-cycloalkylsulfonyl, (C₄-C₈)-cycloalkenylsulfonyl, (C₃-C₈)-halocycloalkylsulfonyl, (C₄-C₈)-halocycloalkenylsulfonyl, (C₁-C₆)-alkylamino, (C₂-C₆)-alkenylamino, (C₂-C₆)-alkynylamino, (C₁-C₆)-haloalkylamino, (C₂-C₆)-haloalkenylamino, (C₂-C₆)-haloalkynylamino, (C₃-C₈)-cycloalkylamino, (C₄-C₈)-cycloalkenylamino, (C₃-C₈)-halocycloalkylamino and (C₄-C₈)-halocycloalkenylamino.

R and R¹-R⁸ are particularly preferably H, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, heterocyclyl, where the four last-mentioned radicals are unsubstituted or substituted by one or more, preferably by one to four, radicals from the group consisting of halogen, preferably F, CN, SiMe₃, —O—(C₁-C₆)-alkyl, —S—(C₁-C₆)-alkyl or —O—CO—(C₁-C₆)-alkyl.

Very particular preference is given to compounds of the formulae I′-1 to 1′-32, also in the form of their pyridine N-oxides, where the symbols and indices are as defined above:

Preference is likewise given to the corresponding formulae I′-33 to I′-96 in which Y is —CH₂CH₂—, —CH₂—CH(CH₃)—, —CH₂—CH₂—CH₂— and —CH₂—C(CH₃)₂—.

The term “halogen” includes fluorine, chlorine, bromine and iodine.

The term “(C₁-C₄)-alkyl” is to be understood as a straight-chain or branched hydrocarbon radical having 1, 2, 3 or 4 carbon atoms, such as, for example, the methyl, ethyl, propyl, isopropyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl radical. Correspondingly, alkyl radicals having a greater range of carbon atoms are to be understood as straight-chain or branched saturated hydrocarbon radicals which contain a number of carbon atoms which corresponds to the range stated. Thus, the term “(C₁-C₆)-alkyl” includes the abovementioned alkyl radicals, and, for example, the pentyl, 2-methylbutyl, 1,1-dimethylpropyl and hexyl radical. The term “(C₁-C₁₀)-alkyl” is to be understood as the abovementioned alkyl radicals, and, for example, the nonyl, 1-decyl or 2-decyl radical.

“(C₁-C₄)-Haloalkyl” is to be understood as an alkyl group mentioned under the term “(C₁-C₄)-alkyl” in which one or more hydrogen atoms are replaced by the same number of identical or different halogen atoms, preferably chlorine or fluorine, such as the trifluoromethyl, the 1-fluoroethyl, the 2,2,2-trifluoroethyl, the chloromethyl, fluoromethyl, the difluoromethyl and the 1,1,2,2-tetrafluoroethyl group.

“(C₁-C₄)-Alkoxy” is to be understood as an alkoxy group whose hydrocarbon radical has the meaning given under the term “(C₁-C₄)-alkyl”. Alkoxy groups embracing a greater range of carbon atoms are to be understood correspondingly.

The terms “alkenyl” and “alkynyl” having a prefix stating the range of carbon atoms denote a straight-chain or branched hydrocarbon radical having a number of carbon atoms corresponding to the range stated which comprises at least one multiple bond which may be in any position of the unsaturated radical in question. “(C₂-C₄)-Alkenyl” is thus, for example, the vinyl, allyl, 2-methyl-2-propene or 2-butenyl group; “(C₂-C₆)-alkenyl” denotes the abovementioned radicals and, for example, the pentenyl, 2-methylpentenyl or the hexenyl group. “(C₂-C₄)-Alkynyl” is, for example, the ethynyl, propargyl, 2-methyl-2-propyne or 2-butynyl group. “(C₂-C₆)-Alkynyl” is to be understood as the abovementioned radicals and, for example, the 2-pentynyl or the 2-hexynyl group and “(C₂-C₁₀)-alkynyl” is to be understood as the abovementioned radicals and, for example, the 2-octynyl or the 2-decynyl group.

“(C₃-C₈)-Cycloalkyl” denotes monocyclic alkyl radicals, such as the cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl radical and bicyclic alkyl radicals, such as the norbornyl radical.

The term “(C₃-C₈)-cycloalkyl-(C₁-C₄)-alkyl” is to be understood as, for example, the cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclohexylethyl and cyclohexylbutyl radical, and the term “(C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl is to be understood as, for example, the 1-methylcyclopropyl, 1-methylcyclopentyl, 1-methylcyclohexyl, 3-hexylcyclobutyl and 4-tert-butyl-cyclohexyl radical.

“(C₁-C₄)-Alkoxy-(C₁-C₆)-alkyloxy” is an alkoxy group as defined above which is substituted by a further alkoxy group, such as, for example, 1-ethoxyethoxy.

“(C₃-C₈)-Cycloalkoxy” or “(C₃-C₈)-cycloalkylthio” is to be understood as one of the abovementioned (C₃-C₈)-cycloalkyl radicals which is linked via an oxygen or sulfur atom.

“(C₃-C₈)-Cycloalkyl-(C₁-C₆)-alkoxy” is, for example, the cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclohexylethoxy or the cyclohexylbutoxy group.

The term “(C₁-C₄)-alkyl-(C₃-C₈)-cycloalkoxy” is, for example, the methylcyclopropyloxy, methylcyclobutyloxy or the butylcyclohexyloxy group.

“(C₁-C₆)-Alkylthio” is an alkylthio group whose hydrocarbon radical has the meaning given under the term “(C₁-C₆)-alkyl”.

Correspondingly, “(C₁-C₆)-alkylsulfinyl” is, for example, the methyl-, ethyl-, propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl- or tert-butylsulfinyl group and “(C₁-C₆)-alkylsulfonyl” is, for example, the methyl-, ethyl-, propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl- or tert-butylsulfonyl group.

“(C₁-C₆)-Alkylamino” is a nitrogen atom which is substituted by one or two identical or different alkyl radicals of the above definition.

The term “(C₁-C₆)-mono- or -dialkylcarbamoyl” is a carbamoyl group having one or two hydrocarbon radicals which have the meaning given under the term “(C₁-C₆-alkyl)” and which, in the case of two hydrocarbon radicals, may be identical or different.

Correspondingly, “(C₁-C₆)-dihaloalkylcarbamoyl” is a carbamoyl group which carries two (C₁-C₆)-haloalkyl radicals in accordance with the above definition or one (C₁-C₆)-haloalkyl radical and one (C₁-C₆)-alkyl radical in accordance with the above definition.

“(C₁-C₆)-Alkanoyl” is, for example, the acetyl, propionyl, butyryl or 2-methylbutyryl group.

The term “aryl” is to be understood as a carbocyclic, i.e. constructed from carbon atoms, aromatic radical preferably having 6 to 14, in particular 6 to 12, carbon atoms, such as, for example, phenyl, naphthyl or biphenylyl, preferably phenyl. “Aroyl” is thus an aryl radical as defined above which is attached via a carbonyl group, such as, for example, the benzoyl group.

The term “heterocyclyl” preferably denotes a cyclic radical which may be fully saturated, partially unsaturated or fully unsaturated and which may be interrupted by at least one or more identical or different atoms from the group consisting of nitrogen, sulfur or oxygen, two oxygen atoms, however, not being allowed to be directly adjacent to one another and at least one carbon atom having to be present in the ring, such as, for example, a thiophene, furan, pyrrole, thiazole, oxazole, imidazole, isothiazole, isoxazole, pyrazole, 1,3,4-oxadiazole, 1,3,4-thiadiazole, 1,3,4-triazole, 1,2,4-oxadiazole, 1,2,4-thiadiazole, 1,2,4-triazole, 1,2,3-triazole, 1,2,3,4-tetrazole, benzo[b]thiophene, benzo[b]furan, indole, benzo[c]thiophene, benzo[c]furan, isoindole, benzoxazole, benzothiazole, benzimidazole, benzisoxazole, benzisothiazole, benzopyrazole, benzothiadiazole, benzotriazole, dibenzofuran, dibenzothiophene, carbazole, pyridine, pyrazine, pyrimidine, pyridazine, 1,3,5-triazine, 1,2,4-triazine, 1,2,4,5-tetrazine, quinoline, isoquinoline, quinoxaline, quinazoline, cinnoline, 1,8-naphthyridine, 1,5-naphthyridine, 1,6-naphthyridine, 1,7-naphthyridine, phthalazine, pyridopyrimidine, purine, pteridine, 4H-quinolizine; piperidine, pyrrolidine, oxazoline, tetrahydrofuran, tetrahydropyran, isoxazolidine or thiazolidine radical. The term “heteroaromatic” thus embraces, from among the meanings mentioned above under “heterocyclyl”, in each case the fully unsaturated aromatic heterocyclic compounds.

Heterocyclyl is particularly preferably a saturated, partially saturated or aromatic ring system having 3 to 6 ring members and 1 to 4 heteroatoms from the group consisting of O, S and N, wherein at least one of the ring members is carbon.

Heterocyclyl is very particularly preferably a radical of pyridine, pyrimidine, (1,2,4)-oxadiazole, (1,3,4)-oxadiazole, pyrrole, furan, thiophene, oxazole, thiazole, imidazole, pyrazole, isoxazole, 1,2,4-triazole, tetrazole, pyrazine, pyridazine, oxazoline, thiazoline, tetrahydrofuran, tetrahydropyran, morpholine, piperidine, piperazine, pyrroline, pyrrolidine, oxazolidine, thiazolidine, oxirane and oxetane.

“Aryl-(C₁-C₄)-alkoxy” is an aryl radical which is attached via a (C₁-C₄)-alkoxy group, for example the benzyloxy, phenylethoxy, phenylbutoxy or naphthylmethoxy radical.

“Arylthio” is an aryl radical attached via a sulfur atom, for example the phenylthio or the 1- or 2-naphthylthio radical. Correspondingly, “aryloxy” is, for example, the phenoxy or 1- or 2-naphthyloxy radical.

“Aryl-(C₁-C₄)-alkylthio” is an aryl radical which is attached via an alkylthio radical, for example the benzylthio, naphthylmethylthio or the phenylethylthio radical.

The term “(C₁-C₆)-trialkylsilyl” denotes a silicon atom which carries three identical or different alkyl radicals in accordance with the above definition. Correspondingly “aryl-(C₁-C₆)-dialkylsilyl” is a silicon atom which carries one aryl radical and two identical or different alkyl radicals in accordance with the above definition, “diaryl-(C₁-C₆)-alkylsilyl” is a silicon atom which carries one alkyl radical and two identical or different aryl radicals in accordance with the above definition, and “triarylsilyl” is a silicon atom which carries three identical or different aryl radicals in accordance with the above definition.

In cases where two or more radicals R⁹ are present in a substituent, such as, for example, in —C(═W)NR⁹ ₂, these radicals may be identical or different.

Depending on the nature of the substituents defined above, the compounds of the formula (I′) have acidic or basic properties and can form salts. If the compounds of the formula (I′) carry, for example, groups such as hydroxyl, carboxyl or other groups inducing acidic properties, these compounds can be reacted with bases to give salts. Suitable bases are, for example, hydroxides, carbonates, bicarbonates of the alkali metals and alkaline earth metals, in particular those of sodium, potassium, magnesium and calcium, further ammonia, primary, secondary and tertiary amines having (C₁-C₄)-alkyl radicals and also mono-, di- and trialkanolamines of (C₁-C₄)-alkanols. If the compounds of the formula (I′) carry, for example, groups such as amino, alkylamino or other groups inducing basic properties, these compounds can be reacted with acids to give salts. Suitable acids are, for example, mineral acids, such as hydrochloric acid, sulfuric acid and phosphoric acid, organic acids, such as acetic acid and oxalic acid, and acidic salts, such as NaHSO₄ and KHSO₄. The salts which can be obtained in this manner likewise have insecticidal, acaricidal and nematicidal properties.

The compounds of the formula (I′) may have one or more asymmetric carbon atoms or stereoisomers on double bonds. Enantiomers or diastereomers may therefore be present. The invention embraces both the pure isomers and mixtures thereof. The mixtures of diastereomers can be separated into the isomers by customary methods, for example by selective crystallization from suitable solvents or by chromatography. Racemates can be separated into the enantiomers by customary methods.

The compounds according to the invention are prepared according to methods which are known per se from the literature, as described in standard works on organic synthesis, for example Houben-Weyl, Methoden der Organischen Chemie [Methods of Organic Chemistry], Georg-Thieme-Verlag, Stuttgart.

The preparation is carried out under reaction conditions which are known and suitable for the reactions mentioned. It is also possible to employ variants which are known per se but not mentioned in more detail here.

If desired, the starting materials can also be formed in situ, such that they are not isolated from the reaction mixture but are immediately reacted further to give the compounds of the formula (I′).

For preparing compounds of the formula (I′), for example, activated derivatives of the acid of the formula (II′),

are reacted in the presence of a base with a compound of the formula (III′),

in which the radical X—Y—R is as defined in formula (I′) or corresponds to a precursor of such a radical. The activated derivative used can be, for example, an acyl halide, an ester or an anhydride. Suitable bases are amines, such as triethylamine, diisopropylethylamine, pyridine or lutidine, alkali metal hydroxides, alkali metal alkoxides, such as sodium ethoxide or potassium tert-butoxide, or alkyl metal compounds, such as butyllithium.

Depending on the conditions selected, the described reaction can be carried out as a one-step process or as a two-step process, the intermediates being compounds of the formula (IV′):

Compounds of the formula (IV′) can be cyclized to the 1,2,4-oxadiazoles by heating in an inert solvent at temperatures of up to 180° C. and by addition of dehydrating agents (for example Amberlyst).

Compounds of the formula (IV′) are also directly obtainable from the acid of the formula (II′) and amidoximes of the formula (III′) by using a dehydrating agent, such as dicyclohexylcarbodiimide, 1-ethyl-3-(3-dimethylamino-propyl)carbodiimide or N,N′-carbonyldiimidazole.

Both trifluoromethylnicotinic acid (II′) and amidoximes of the formula (III′) are commercially available or can be prepared by processes known from the literature (see, for example: Houben-Weyl, Methoden der organischen Chemie, Volume X/4, pages 209-212; EP-A 0 580 374; G. F. Holland, J. N. Pereira, J. Med. Chem., 1967, 10, 149).

After the oxadiazolyl group has been constructed, as shown in the following reaction schemes for example by condensation, cyclization or cycloaddition reactions, the radical R can, if desired, be derivatized further, it being possible to employ the broad range of methods of organochemical synthesis.

Central intermediates of ethers, thioethers and analogous derivatives are haloalkyl- or hydroxyalkyl-substituted oxadiazole derivatives of the formula (V′),

which can then be converted into the corresponding target compounds using standard processes of organic synthesis.

Ethers of the formula (I′) are obtainable by etherifying corresponding hydroxyl compounds where the hydroxyl compound is advantageously initially converted into a corresponding metal derivative, for example into the corresponding alkali metal alkoxide by treatment with NaH, NaNH₂, NaOH, KOH, Na₂CO₃. The alkali metal alkoxide or alkali metal phenolate can then be reacted with the appropriate alkyl halide, alkyl sulfonate or dialkyl sulfate, advantageously in an inert solvent, such as acetone, 1,2-dimethoxyethane, DMF or dimethyl sulfoxide, or else in an excess of aqueous or aqueous-alcoholic NaOH or KOH, at temperatures between about 20° C. and 100° C.

Derivatives of the amino compound (VI′) can be prepared, for example, by reacting the chloro compound ((V′), V′=Cl) with amines or via the central intermediate ((V′); V′=NH₂).

The synthesis of the central intermediate ((V′); V′=NH₂) is effected by reacting the chloro derivative ((V′; V=Cl) with ammonia in the presence of a suitable base or, preferably by reacting the chloro derivative ((V′); V′=Cl) with potassium phthalimide and subsequent hydrazinolysis. Further derivatisation of this central intermediate ((V′); V′=NH₂) is effected by the reaction with suitable electrophiles.

For preparing the sulfoxides ((VII′); n=1) and the sulfones ((VII′); n=2), the corresponding thioethers of the formula (VII′) (n=0) are, for example, employed:

The synthesis is carried out by oxidation with an oxidizing agent, for example meta-chloroperbenzoic acid, with an appropriately selected stoichiometry and temperature.

The synthesis of alkylester substituted oxadiazol derivatives (VIII′) is effected, e.g. by the substitution of chlorine in ((V′); V′=Cl) by alkalicarboxylates or the esterification of the hydroxyalkyl-oxadiazol ((V′); V′=OH) with activated derivatives of carboxylic acids.

Starting from the hydroxyalkyl oxadiazol ((V′); V′=OH) the respective sulfonates can be prepared analogously:

To prepare sulfonamides (X′) the chloroalkyl compound ((V′); V′=Cl) is converted to the respective sodium sulfonate (IX′) with the acid of sodium sulfite, which the can be further derivatized to the desired sulfonamide (X′).

Collections of compounds of the formula (I′) which can be synthesized by the abovementioned scheme may also be prepared in a parallel manner and this may be effected manually or in a semiautomated or fully automated manner. In this case, it is possible, for example, to automate the procedure of the reaction, the work-up or the purification of the products or of the intermediates. In total, this is to be understood as meaning a procedure as is described, for example, by S. H. DeWitt in “Annual Reports in Combinatorial Chemistry and Molecular Diversity: Automated Synthesis”, Volume 1, Verlag Escom 1997, pages 69 to 77.

A number of commercially available apparatuses as they are offered by, for example, Stem Corporation, Woodrolfe Road, Tollesbury, Essex, CM9 8SE, England, H+P Labortechnik GmbH, Bruckmannring 28, 85764 Oberschleiβheim, Germany or Radleys, Shirehill, Saffron Walden, Essex, England may be used for the parallel procedure of the reaction and work-up. For the parallel purification of compounds of the formula (I′), or of intermediates obtained during the preparation, use may be made, inter alia, of chromatography apparatuses, for example those from ISCO, Inc., 4700 Superior Street, Lincoln, Nebr. 68504, USA.

The apparatuses mentioned lead to a modular procedure in which the individual process steps are automated, but manual operations have to be performed between the process steps. This can be avoided by employing semi-integrated or fully integrated automation systems where the automation modules in question are operated by, for example, robots. Such automation systems can be obtained, for example, from Zymark Corporation, Zymark Center, Hopkinton, Mass. 01748, USA.

In addition to what has been described here, compounds of the formula (I′) may be prepared in part or fully by solid-phase-supported methods. For this purpose, individual intermediate steps or all intermediate steps of the synthesis or of a synthesis adapted to suit the procedure in question are bound to a synthetic resin. Solid-phase-supported synthesis methods are described extensively in the specialist literature, for example Barry A. Bunin in “The Combinatorial Index”, Verlag Academic Press, 1998.

The use of solid-phase-supported synthesis methods permits a series of protocols which are known from the literature and which, in turn, can be performed manually or in an automated manner. For example, the “tea-bag method” (Houghten, U.S. Pat. No. 4,631,211; Houghten et al., Proc. Natl. Acad. Sci, 1985, 82, 5131-5135), in which products from IRORI, 11149 North Torrey Pines Road, La Jolla, Calif. 92037, USA, are employed, may be semiautomated. The automation of solid-phase-supported parallel syntheses is performed successfully, for example, by apparatuses from Argonaut Technologies, Inc., 887 Industrial Road, San Carlos, Calif. 94070, USA or MultiSynTech GmbH, Wullener Feld 4, 58454 Witten, Germany.

The preparation according to the processes described herein yields compounds of the formula (I′) in the form of substance collections which are referred to as libraries. The present invention also relates to libraries which comprise at least two compounds of the formula (I′).

The compounds of the formula (I′) are suitable for controlling animal pests, in particular insects, arachnids, helminths and mollusks, very especially preferably for controlling insects and arachnids, which are encountered in agriculture, in livestock breeding, in forests, in the protection of stored goods and materials and in the hygiene sector, and have good plant tolerance and favorable toxicity to warm-blooded species. They are active against normally sensitive and resistant species and against all or individual development stages. The abovementioned pests include:

From the order of the Acarina, for example, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Eotetranychus spp., Oligonychus spp. and Eutetranychus spp.

From the order of the Isopoda, for example, Oniscus asselus, Armadium vulgare and Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus carpophagus and Scutigera spp.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Orthoptera, for example, Blatta orientalis, Periplaneta americana, Leucophaea madeira, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis and Schistocerca gregaria.

From the order of the Isoptera, for example, Reticulitermes spp.

From the order of the Anoplura, for example, Phylloera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp. and Linognathus spp.

From the order of the Mallophaga, for example, Trichodectes spp. and Damalinea spp.

From the order of the Thysanoptera, for example, Hercinothrips femoralis and Thrips tabaci.

From the order of the Heteroptera, for example, Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus and Triatoma spp.

From the order of the Homoptera, for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelus bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. and Psylla spp.

From the order of the Lepidoptera, for example, Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Laphygma exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima and Tortrix viridana.

From the order of the Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylloides chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonumus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrynchus assimilis, Hypera postica, Dermestes spp., Trogoderma, Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis and Costelytra zealandica.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythiocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hypobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae and Tipula paludosa.

From the order of the Siphonaptera, for example, Xenopsylla cheopsis and Ceratophyllus spp.

From the order of the Arachnida, for example, Scorpio maurus and Latrodectus mactans.

From the class of helminths, for example, Haemonchus, Trichostrongulus, Ostertagia, Cooperia, Chabertia, Strongyloides, Oesophagostomum, Hyostrongulus, Ancylostoma, Ascaris and Heterakis, as well as Fasciola.

From the class of the Gastropoda, for example, Deroceras spp., Arion spp., Lymnaea spp., Galba spp., Succinea spp., Biomphalaria spp., Bulinus spp. and Oncomelania spp.

From the class of Bivalva, for example, Dreissena spp.

The phytoparasitic nematodes which can be controlled according to the invention include, for example, the root-parasitic soil nematodes, such as, for example, those of the genera Meloidogyne (root gall nematodes, such as Meloidogyne incognita, Meloidogyne hapla and Meloidogyne javanica), Heterodera and Globodera (cyst-forming nematodes, such as Globodera rostochiensis, Globodera pallida and Heterodera trifolii) and of the genera Radopholus, such as Radopholus similis, Pratylenchus, such as Pratylenchus neglectus, Pratylenchus penetrans and Pratylenchus curvitatus; Tylenchulus, such as Tylenchulus semipenetrans, Tylenchorhynchus, such as Tylenchorhynchus dubius and Tylenchorhynchus claytoni, Rotylenchus, such as Rotylencus robustus, Heliocotylenchus, such as Heliocotylenchus multicinctus, Belonoaimus, such as Belonoaimus longicaudatus, Longidorus, such as Longidorus elongatus, Trichodorus, such as Trichodorus primitivus and Xiphinema, such as Xiphinema index.

The nematode genera Ditylenchus (stem parasites, such as Ditylenchus dipsaci and Ditylenchus destructor), Aphelenchoides (leaf nematodes, such as Aphelenchoides ritzemabosi) and Anguina (blossom nematodes, such as Anguina tritici) can furthermore be controlled with the compounds according to the invention.

The invention also relates to compositions, for example crop protection compositions, preferably insecticidal, acaricidal, ixodicidal, nematicidal, molluskidal or fungicidal, particularly preferably insecticidal and acaricidal compositions, which comprise one or more compounds of the formula (I′) in addition to suitable formulation auxiliaries.

In general, the compositions according to the invention comprise from 1 to 95% by weight of the active compounds of the formula (I′).

For preparing the compositions according to the invention, the active compound and the other additives are combined and formulated as a suitable use form.

The invention also relates to compositions, in particular insecticidal and acaricidal compositions, which comprise the compounds of the formula (I′) in addition to suitable formulation auxiliaries.

The compositions according to the invention in general comprise from 1 to 95% by weight the active compounds of the formula (I′). They can be formulated in various ways, depending on how this is determined by the biological and/or chemico-physical parameters. Suitable formulation possibilities are therefore:

Wettable powders (WP), emulsifiable concentrates (EC), aqueous solutions (SL), emulsions, sprayable solutions, oil- or water-based dispersions (SC), suspoemulsions (SE), dusting powders (DP), seed dressings, granules in the form of microgranules, sprayed granules, absorption granules and adsorption granules, water-dispersible granules (WG), ULV formulations, microcapsules, waxes or baits.

These individual types of formulation are known in principle and are described, for example, in: Winnacker-Küchler, “Chemische Technologie” [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th Edition 1986; van Falkenberg, “Pesticides Formulations”, Marcel Dekker N.Y., 2nd Edition 1972-73; K. Martens, “Spray Drying Handbook”, 3rd Edition 1979, G. Goodwin Ltd. London.

The necessary formulation auxiliaries, i.e. carrier substances and/or surface-active substances, such as inert materials, surfactants, solvents and further additives, are likewise known and are described, for example, in: Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2nd Edition, Darland Books, Caldwell N.J.; H. v. Olphen, “Introduction to Clay Colloid Chemistry”, 2nd Edition, J. Wiley & Sons, N.Y.; Marsden, “Solvents Guide”, 2nd Edition, Interscience, N.Y. 1950; McCutcheon's, “Detergents and Emulsifiers Annual”, MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface Active Agents”, Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, “Grenzflächenaktive Äthylenoxidaddukte” [Surface-active ethylene oxide adducts], Wiss. Verlagsgesell., Stuttgart 1967; Winnacker-Küchler, “Chemische Technologie” [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th Edition 1986.

Combinations with other substances having a pesticidal action, fertilizers and/or growth regulators can be prepared on the basis of these formulations, for example in the form of a ready-to-use formulation or as a tank mix. Wettable powders are preparations which are uniformly dispersible in water and which, alongside the active compound, and in addition to a diluent or inert substance, also comprise wetting agents, for example polyethoxylated alkylphenols, polyethoxylated fatty alcohols or alkyl- or alkylphenolsulfonates, and dispersing agents, for example sodium ligninsulfonate or sodium 2,2′-dinaphthylmethane-6,6′-disulfonate. Emulsifiable concentrates are prepared by dissolving the active compound in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or also higher-boiling aromatics or hydrocarbons, with the addition of one or more emulsifiers.

Emulsifiers which can be used are, for example: calcium alkylarylsulfonates, such as Ca dodecylbenzenesulfonate, or nonionic emulsifiers, such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide condensation products, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylene sorbitol esters.

Dusting powders are obtained by grinding the active compound with finely divided solid substances, for example talc, naturally occurring clays, such as kaolin, bentonite and pyrophillite, or diatomaceous earth. Granules can be prepared either by spraying the active compound onto granular inert material capable of adsorption or by applying active compound concentrates to the surface of carrier substances, such as sand, kaolinites or granular inert material, by means of adhesives, for example polyvinyl alcohol, sodium polyacrylate or mineral oils. Suitable active compounds can also be granulated in the manner customary for the preparation of fertilizer granules—if desired as a mixture with fertilizers.

In wettable powders, the active compound concentration is generally about 10 to 90% by weight, the remainder to make up 100% by weight comprising customary formulation constituents. In emulsifiable concentrates, the active compound concentration can be about 5 to 80% by weight. Dust-like formulations usually comprise 5 to 20% by weight of active compound, and sprayable solutions about 2 to 20% by weight. In granules, the content of active compound partly depends on whether the active compound is present in liquid or solid form and what granulating auxiliaries, fillers and the like are used.

In addition, the active compound formulations mentioned comprise, if appropriate, the particular customary tackifiers, wetting agents, dispersing agents, emulsifiers, penetration agents, solvents, fillers or carrier substances.

For use, the concentrates in the commercially available form are diluted in the customary manner, if appropriate, for example by means of water in the case of wettable powders, emulsifiable concentrates, dispersions and in some cases also microgranules. Dust-like and granular formulations as well as sprayable solutions are usually not diluted further with additional inert substances before use.

The required amount applied varies with the external conditions, such as temperature, humidity and the like. It can vary within wide limits, for example between 0.0005 and 10.0 kg/ha or more of active substance, but is preferably between 0.001 and 5 kg/ha of active compound.

The active compounds according to the invention can be present in their commercially available formulations and in the use forms prepared from these formulations as mixtures with other active compounds, such as insecticides, attractants, sterilizing agents, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.

The pesticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, formamidines, tin compounds and substances produced by microorganisms.

Preferred partners for the mixtures are:

1. from the group of phosphorus compounds

acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, bromophos, bromophos-ethyl, cadusafos (F-67825), chlorethoxyphos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, demeton, demeton-S-methyl, demeton-S-methyl sulfone, dialifos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, EPN, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitriothion, fensulfothion, fenthion, fonofos, formothion, fosthiazate (ASC-66824), heptenophos, isazophos, isothioate, isoxathion, malathion, methacrifos, methamidophos, methidathion, salithion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosfolan, phosphocarb (BAS-301), phosmet, phosphamidon, phoxim, pirimiphos, primiphos-ethyl, pirimiphos-methyl, pro fenofos, propaphos, proetamphos, prothiofos, pyraclofos, pyridapenthion, quinaiphos, sulprofos, temephos, terbufos, tebupirimfos, tetrachlorvinphos, thiometon, triazophos, trichlorphon, vamidothion;

2. from the group of carbamates

alanycarb (OK-135), aldicarb, 2-sec-butylphenyl methylcarbamate (BPMC), carbaryl, carbofliran, carbosulfan, cloethocarb, benfuiracarb, ethiofencarb, furathiocarb, HCN-801, isoprocarb, methomyl, 5-methyl-m-cumenyl butyryl(methyl)carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, 1-methylthio(ethylideneamino) N-methyl-N-(morpholinothio)carbamate (UC 51717), triazamate;

3. from the group of carboxylic acid esters

acrinathrin, allethrin, alphametrin, 5-benzyl-3-furyl methyl (E)-(1R)-cis-2,2-di-methyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate, beta-cyfluthrin, beta-cypermethrin, bioallethrin, bioallethrin ((S)-cyclopentyl isomer), bioresmethrin, bifenthrin, (RS)-1-cyano-1-(6-phenoxy-2-pyridyl)methyl (1RS)-trans-3-(4-tert-butylphenyl)-2,2-dimethylcyclopropanecarboxylate (NCI 85193), cycloprothrin, cyfluthrin, cyhalothrin, cythithrin, cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, fenfluthrin, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (D isomer), imiprothrin (S-41311), lambda-cyhalothrin, permethrin, pheothrin ((R) isomer), prallethrin, pyrethrins (natural products), resmethrin, tefluthrin, tetramethrin, theta-cypermethrin (TD-2344), tralomethrin, transfluthrin and zeta-cypermethrin (F-56701);

4. from the group of amidines

amitraz, chlordimeform;

5. from the group of tin compounds

cyhexatin, fenbutatin oxide;

6. others

abamectin, ABG-9008, acetamiprid, Anagrapha falcitera, AKD-1022, AKD-3059, ANS-118, Bacillus thuringiensis, Beauveria bassianea, bensultap, bifenazate (D-2341), binapacryl, BJL-932, bromopropylate, BTG-504, BTG-505, buprofezin, camphechlor, cartap, chlorobenzilate, chlorfenapyr, chlorfluazuron, 2-(4-chlorophenyl)-4,5-diphenylthiophene (UBI-T 930), chlorfentezine, chromafenozide (ANS-118), CG-216, CG-217, CG-234, A-184699, 2-naphthylmethyl cyclopropanecarboxylate (Ro 12-0470), cyromazin, diacloden (thiamethoxam), diafenthiuron, N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propyloxy)phenyl)carbamoyl)-2-chlorobenzocarboxamide acid ethyl ester, DDT, dicofol, diflubenzuron, N-(2,3-dihydro-3-methyl-1,3-thiazol-2-ylidene)-2,4-xylidine, dinobuton, dinocap, diofenolan, DPX-062, emamectin-benzoate (MK-244), endosulfan, ethiprole (sulfethiprole), ethofenprox, etoxazole (YI-5301), fenazaquin, fenoxycarb, fipronil, fluazuron, flumite (flufenzine, SZI-121), 2-fluoro-5-(4-(4-ethoxyphenyl)-4-methyl-1-pentyl)diphenyl ether (MTI 800), granulosis and nuclear polyhedrosis viruses, fenpyroximate, fenthiocarb, flubenzimine, flucycloxuron, flufenoxuron, flufenprox (ICI-A5683), fluproxyfen, gamma-HCH, halofenozide (RH-0345), halofenprox (MTI-732), hexaflumuron (DE_(—)473), hexythiazox, HOI-9004, hydramethylnon (AC 217300), lufenuron, imidacloprid, indoxacarb (DPX-MP062), kanemite (AKD-2023), M-020, MTI-446, ivermectin, M-020, methoxyfenozide (Intrepid, RH-2485), milbemectin, NC-196, neemgard, nitenpyram (TI-304), 2-nitromethyl-4,5-dihydro-6H-thiazine (DS 52618), 2-nitromethyl-3,4-dihydrothiazole (SD 35651), 2-nitromethylene-1,2-thiazinan-3-ylcarbamaldehyde (WL 108477), pyriproxyfen (S-71639), NC-196, NC-1111, NNI-9768, novaluron (MCW-275), OK-9701, OK-9601, OK-9602, propargite, pymethrozine, pyridaben, pyrimidifen (SU-8801), RH-0345, RH-2485, RYI-210, S-1283, S-1833, SB7242, SI-8601, silafluofen, silomadine (CG-177), spinosad, SU-9118, tebufenozide, tebufenpyrad (MK-239), teflubenzuron, tetradifon, tetrasul, thiacloprid, thiocyclam, TI-435, tolfenpyrad (OMI-88), triazamate (RH-7988), triflumuron, verbutin, vertalec (Mykotal), YI-5301,

The abovementioned combination partners are known active compounds, and most of them are described in Ch. R. Worthing, S. B. Walker, The Pesticide Manual, 11th Edition, British Crop Protection Council Farnham 1997.

The active compound content of the use forms prepared from the commercially available formulations can be from 0.00000001 to 95% by weight of active compound, preferably between 0.00001 and 1% by weight.

The active compounds are used in a customary manner appropriate for the use forms.

The active compounds according to the invention are also suitable for controlling endo- and ectoparasites in the veterinary medicine field and in the field of animal husbandry. The active compounds according to the invention are used here in a known manner, such as by oral use in the form of, for example, tablets, capsules, potions or granules, by means of dermal use in the form of, for example, dipping, spraying, pouring-on, spotting-on and dusting, and by parenteral use in the form of, for example, injection.

The novel compounds of the formula (I′) can accordingly also particularly advantageously be used in livestock husbandry (for example cattle, sheep, pigs and poultry, such as chickens, geese and the like). In a preferred embodiment of the invention, the compounds are administered orally to the animals, if appropriate in suitable formulations and if appropriate with the drinking water or feed. Since excretion in the feces takes place in an active manner, the development of insects in the feces of the animals can be prevented very easily in this way. The dosages and formulations suitable in each case depend in particular on the species and the development stage of the stock animals and also on the level of infestation, and can easily be determined and specified by the customary methods. The compounds can be employed in cattle, for example, in dosages of 0.01 to 1 mg/kg of body weight.

In addition to the application methods mentioned hereinabove, the active compounds of the formula (I′) according to the invention also have excellent systemic action. The active compounds can therefore also be introduced into the plants via below-ground and above-ground parts of plants (root, stem, leaf), when the active compounds are applied in liquid or solid form to the immediate surroundings of the plants (for example granules in soil application, application in flooded rice fields).

Furthermore, the active compounds according to the invention are particularly useful for treating vegetative and generatative propagation stock, such as, for example, seed of, for example, cereals, vegetables, cotton, rice, sugar beet and other crops and ornamentals, of bulbs, cuttings and tubers of other vegetatively propagated crops and ornamentals. To this end, treatment can be carried out prior to sowing or planting (for example by special seed coating techniques, by seed dressings in liquid or solid form or by seed box treatment), during sowing or planting or after sowing or planting by special application techniques (for example seed row treatment). Depending on the application, the amount of active compound applied can vary within a relatively wide range. In general, the application rates are between 1 g and 10 kg of active compound per hectare of soil area.

The compounds of the formula (I′) can also be used for controlling harmful plants in crops of known genetically modified plants or of genetically modified plants still to be developed. The transgenic plants generally have particularly advantageous properties, for example resistance to certain crop protection agents, resistance to plant diseases or pathogens of plant diseases, such as certain insects or microorganisms, such as fungi, bacteria or viruses. Other special properties relate, for example, to the harvested product, with respect to quantity, quality, shelf-life, composition and special ingredients. Thus, transgenic plants having increased starch content or a modified quality of the starch or those having a different fatty acid composition of the harvested product are known.

Preference is given to the use in economically important transgenic crops of useful and ornamental plants, for example cereals, such as wheat, barley, rye, oats, millet, rice, manioc and maize, or else crops of sugar beet, cotton, soya, rapeseed, potato, tomato, pea and other vegetable species.

The use in transgenic crops, in particular crops with resistance to insects, is, in addition to the effects with respect to harmful organisms which can be observed in other crops, frequently associated with effects which are specific for the application in the respective transgenic crop, for example a modified or specifically widened spectrum of pests which can be controlled, or modified application rates which can be used for the application.

The invention therefore also provides the use of compounds of the formula (I′) for controlling harmful organisms in transgenic crop plants.

The use of the compounds according to the invention comprises, in addition to direct application to the pests, any other application where the compounds of the formula (I′) act on the pests. Such indirect applications may be, for example, the use of compounds which decompose or are degraded to compounds of the formula (I′), for example in the soil, the plant or the pest.

Herewith, express reference is made to the content of German Patent Application 198 581 93.9, the priority of which is claimed by the present application, and to the content of the enclosed summary; they are incorporated into this description by reference.

The examples below serve to illustrate the invention.

EXAMPLES I. COMPOUNDS OF FORMULA (I)

A. Formulation Examples

a) A dusting powder is obtained by mixing 10 parts by weight of active compound and 90 parts by weight of talc, as the inert substance, and comminuting the mixture in an impact mill.

b) A wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of active compound, 65 parts by weight of kaolin-containing quartz, as the inert substance, 10 parts by weight of potassium ligninsulfonate and 1 part by weight of sodium oleoylmethyltauride, as wetting and dispersing agent and grinding the mixture in a pinned disk mill.

c) A dispersion concentrate which is readily dispersible in water is prepared by mixing 40 parts by weight of active compound with 7 parts by weight of a sulfosuccinic monoester, 2 parts by weight of a sodium ligninsulfonate and 51 parts by weight of water and grinding the mixture to a fineness of below 5 microns in a grinding bead mill.

d) An emulsifiable concentrate can be prepared from 15 parts by weight of active compound, 75 parts by weight of cyclohexane, as the solvent, and 10 parts by weight of ethoxylated nonylphenol (10 EO), as the emulsifier.

e) Granules can be prepared from 2 to 15 parts by weight of active compound and an inert granule carrier material, such as attapulgite, pumice granules and/or quartz sand. A suspension of the wettable powder from Example b) having a solids content of 30% is expediently used, and this is sprayed onto the surface of attapulgite granules and the components are dried and mixed intimately. The weight content of the wettable powder is approximately 5% and that of the inert carrier material is approximately 95% of the finished granules.

B. Chemical Examples

Example No. 1

3-Isopropyl-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole (Table 1, No. 81)

2 g of methyl 4-trifluoromethylnicotinate and 1.56 g of isobutyramide oxime were initially charged in 15 ml of ethanol and cooled to 0° C. 10 ml of a 1.2 molar sodium ethoxide solution were added dropwise to this solution. The mixture was allowed to warm to room temperature over a period of two hours and stirring was then continued at this temperature until the reaction, according to TLC, had ended.

The reaction mixture was concentrated and the residue was taken up in saturated ammonium chloride solution and extracted with diethyl ether. Chromatographic purification of the crude product gave the desired compound as a yellowish oil.

¹H-NMR (CDCl₃, 300 MHz): d=1.41 (d, J=6.9 Hz, 6H), 3.22 (m, 1H), 7.78 (d, J=5 Hz, 1H), 9.02 (d, J=5 Hz, 1H), 9.34 (s, 1H) ppm.

Example No. 2

3-Isopropyl-5-(4-trifluoromethyl-5-pyrimidyl)-1,2,4-oxadiazole (Table 1, No. 189)

2 g of ethyl 4-trifluoromethylpyrimidine-5-carboxylate and 1.56 g of isobutyramide oxime were initially charged in 15 ml of ethanol and cooled to 0° C. 10 ml of a 1.2 molar sodium ethoxide solution were added dropwise to this solution. The mixture was allowed to warm to room temperature over a period of one hour and then heated under reflux until the reaction, according to TLC, had ended. The reaction mixture was concentrated and the residue was taken up in saturated ammonium chloride solution and extracted with diethyl ether. Chromatographic purification of the crude product gave the desired compound as a yellowish oil.

¹H-NMR (CDCl₃, 300 MHz): d=1.43 (d, J=7 Hz, 6H), 3.22 (hept., J=7 Hz, 1H), 9.52 (s, 1H), 9.58 (s, 1H) ppm.

Example No. 3

2-Methyl-5-(4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazole (Table 3, No. 549)

500 mg of 4-trifluoromethylnicotinic hydrazide were heated under reflux in 3.5 ml of triethyl orthoacetate for 2 hours. The reaction mixture was subsequently concentrated and the residue was carefully admixed with 2 ml of phosphorus oxychloride. The mixture was stirred at room temperature for 1 hour and then poured on ice and extracted with ethyl acetate. Chromatographic purification of the crude product obtained after drying and concentrating gave the desired compound as a yellowish oil.

¹H-NMR (CDCl₃, 300 MHz): d=2.67 (s, 3H), 7.75 (d, J=5 Hz, 1H), 8.99 (d, J=5 Hz, 1H), 9.34 (s, 1H) ppm.

Example No. 4

4-(Ethoxycarbonylmethyl)-2-(4-trifluoromethyl-3-pyridyl)thiazole (Table 4, No. 688)

500 mg of 4-trifluoromethylpyridine-3-thiocarboxamide and 440 mg of ethyl 4-chloroacetate were dissolved in 5 ml of dimethylformamide and heated at 100° C. for 4 hours. After cooling, the reaction mixture was poured onto ice-water and extracted with diethyl ether. The diethyl ether phase was dried (MgSO₄), filtered and concentrated and the residue was purified by chromatography. This gave the desired product in pure form as a colorless oil.

¹H-NMR (CDCl₃, 300 MHz): d=1.28 (t, J=7.5 Hz, 3H), 3.92 (s, 2H), 4.22 (q, J=7.5 Hz, 2H), 7.43 (s, 1H), 7.68 (d, J=5 Hz, 1H), 8.86 (d, J=5 Hz, 1H), 8.97 (s, 1H) ppm.

Example No. 5

4-Ethyl-2-(4-trifluoromethyl-3-pyridyl)oxazole (Table 4, No. 762)

2.6 g of 4-trifluoromethylnicotinic acid were admixed with 20 ml of thionyl chloride and heated at reflux temperature for 1 hour. After cooling, excess thionyl chloride was distilled off and the acyl chloride which remained as a pale yellow oil was taken up in 30 ml of dichloromethane. This solution was subsequently added dropwise to a solution of 2.4 g of 2-amino-1-butanol and 2.75 g of triethylamine in 30 ml of dichloromethane cooled in an ice bath. After the addition had ended, stirring was continued at room temperature for approximately 2 hours. The mixture was poured into ammonium chloride solution and extracted with ethyl acetate. The crude N-(1-hydroxy-2-butyl)-4-trifluoromethylnicotinamide (2.3 g) obtained after drying and concentrating the ethyl acetate phase was dissolved at room temperature in 100 ml dichloromethane and mixed with 4.6 g of periodinan (Dess-Martin reagent). After the reaction had ended, according to TLC, the reaction mixture was concentrated and purified by column chromatography. The resulting 2-(trifluoromethylpyridin-3-amido)butanal (1.5 g) was dissolved in 30 ml of dimethylformamide, admixed with 2.72 g of phosphorus oxychloride and heated at 90° C. for 15 minutes. The solution was then poured onto ice and extracted with diethyl ether. Drying and concentration of the diethyl ether phase and chromatographic purification of the residue gave the product as a brownish oil.

¹H-NMR (CDCl₃, 300 MHz): d=1.3 (t, J=7.4 Hz, 3H), 2.66 (qd, J=7.4 Hz, J<1 Hz, 2H), 7.58 (t, J<1 Hz, 1H), 7.65 (d, J=5 Hz, 1H), 8.83 (d, J=5 Hz, 1H), 9.33 (d, J=5 Hz, 1H) ppm.

Example No. 6

4-Ethyl-2-(4-trifluoromethyl-3-pyridyl)-4,5-dihydrooxazole (Table 5, No 876)

1 g of 4-trifluoromethylnicotinic acid was admixed with 8 ml of thionyl chloride and heated at reflux temperature for 1 hour. After cooling, excess thionyl chloride was distilled off and the acyl chloride which remained as a pale yellow oil was taken up in 10 ml of dichloromethane. This solution was subsequently added dropwise to a solution of 930 mg of 2-amino-1-butanol and 1.06 g of triethylamine in 10 ml of dichloromethane cooled in an ice bath. After the addition had ended, stirring was continued for approximately 2 hours at room temperature. The mixture was poured into an ammonium chloride solution and extracted with ethyl acetate. The crude N-(1-hydroxy-2-butyl)-4-trifluoromethylnicotinamide (1.03 g) obtained after drying and concentration of the ethyl acetate phase was dissolved at room temperature in 6 ml of tetrahydrofuran and admixed with 1.09 g of N-[(triethylammonio)sulfonyl]-methylcarbamate (Burgess' reagent). The mixture was stirred at 60° C. for 3 hours. After cooling, the batch was concentrated and the residue was taken up in water and extracted with ethyl acetate. Chromatographic purification of the crude product gave the product as a colorless oil.

¹H-NMR (CDCl₃, 200 MHz): d=1.03 (t, J=7.6 Hz, 3H), 1.72 (m, 2H), 4.15 (t, J=7.5 Hz, 1H), 4.32 (m, 1H), 4.58 (t, J=7.5 Hz, 1H), 7.6 (d, J=5 Hz, 1H), 8.87 (d, J=5 Hz, 1H), 9.06 (s, 1H) ppm.

Example No. 7

2-(3-Thienylmethyl)-5-(4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazole (Table 3, No. 572)

880 mg of thiophene-3-acetic hydrazide were added to a solution of 960 mg of 4-trifluoromethylpyridine-3-carboxylic acid in 5 ml of phosphorus oxychloride, and the mixture was heated at reflux for 2 hours. The reaction mixture was subsequently added dropwise to ice-water, made neutral using concentrated ammonia solution and extracted with ethyl acetate. Drying (Na₂SO₄), concentration and chromatographic purification gave 624 mg of the desired product as a slightly brown oil.

¹H-NMR (CDCl₃, 200 MHz): d=4.38 (s, 2H), 7.1 (d, J=5 Hz, 1H), 7.23 (s, 1H), 7.37 (dd, J=5 Hz, J=3 Hz, 1H), 7.75 (d, J=6 Hz, 1H), 8.98 (d, J=6 Hz, 1H), 9.36 (s, 1H) ppm.

Example No. 8

5-Methyl-3-(4-trifluoromethyl-3-pyridyl)-1H-1,2,4-triazole (Table 6, No. 947)

A mixture of 290 mg of ethylacetimidate hydrochloride and 100 mg of sodium hydroxide in 2 ml of ethanol was filtered and added to 500 mg of 4-trifluoromethyl-3-pyridinecarbohydrazide, and the mixture was heated under reflux for 3 hours. The reaction mixture was concentrated and the residue was suspended in xylene and refluxed for 4 hours. For work-up, the batch was diluted with ethyl acetate and washed with water. Chromatographic purification gave the pure product as a colorless solid.

¹H-NMR (CDCl₃, 300 MHz): d=2.58 (s, 3H), 7.64 (d, J=5 Hz, 1H), 8.85 (d, J=5 Hz, 1H), 9.19 (s, 1H) ppm.

Example No. 9

3-(N-Isopropylcarbamoylmethyl)-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

Step 1: Tert-butyl 3-Amino-3-(4-trifluoromethyl-3-pyridinecarbonyloxy-imino)propionate

30 g of 4-trifluoromethyl-3-pyridinecarboxylic acid is initially charged in 150 ml of dry THF and, a little at a time, admixed with 25.3 g of carbonyl-diimidazole. The mixture is stirred at room temperature for 30 min. 27.2 g of tert-butoxycarbonylacetamide oxime dissolved in 150 ml of THF are then added dropwise. The mixture is stirred overnight, the solvent is evaporated and the residue is taken up in ethyl acetate, washed three times with 1 M sulfuric acid and once with saturated sodium bicarbonate solution. Concentration of the ethyl acetate phase gives 28 g of the product as a pale yellow solid.

¹H-NMR (CDCl₃, 300MHz): d=1.5 (s, 9H), 3.3 (s, 2H), 5.55 (br.s, 2H), 7.83 (d, J=5 Hz, 1H), 8.97 (d, J=5 Hz, 1H), 9.13 (s, 1H) ppm.

Step 2: 3-(Tert-butoxycarbonylmethyl)-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

28 g of tert-butyl 3-amino-3-(4-trifluoromethyl-3-pyridinecarbonyloxy-imino)propionate are dissolved in 380 ml of toluene and heated under reflux for 17 hours. Concentration and chromatographic purification of the residue over silica gel gives 14.4 g of the product as a pale brown oil.

¹H-NMR (CDCl₃, 300MHz): d=1.5 (s, 9H), 3.88 (s, 2H), 7.79 (d, J=5 Hz, 1H), 9.02 (d, J=5 Hz, 1H), 9.33 (s, 1H) ppm.

Step 3: 3-(Hydroxycarbonylmethyl)-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

12.4 g of 3-(tert-butoxycarbonylmethyl)-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole are dissolved in 110 ml of dichloromethane and admixed with 57 ml of trifluoroacetic acid. The reaction mixture is stirred at room temperature for 1.5 hours and subsequently concentrated under reduced pressure. The residue is repeatedly taken up in dichloromethane and reconcentrated to remove any remaining trifluoroacetic acid. The mixture is finally triturated with diethyl ether, giving 8.1 g of the product as a white solid.

Step 4: 3-(N-Isopropylcarbamoylmethyl)-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

1 g of the product of the previous step are dissolved in 10 ml of THF and is mixed with 0.59 g of carbonyldiimidazole. The mixture is stirred at room temperature for 10 minutes, 0.22 g of isopropylamine are added dropwise and the mixture is allowed to react for a further 1.5 hours at room temperature with stirring. The reaction mixture is subsequently concentrated and the residue is taken up in ethyl acetate and washed three times with 1 M sulfuric acid and once with saturated sodium bicarbonate solution. The solid residue obtained after drying and concentrating the ethyl acetate phase is recrystallized from tert-butyl methyl ether, giving 0.46 g of the pure product as a pale yellow solid.

¹H-NMR (CDCl₃, 300MHz): d=1.20 (d, J=7.6 Hz, 6H), 3.82 (s, 2H), 4.12 (m, 1H), 6.50 (br.s, 1H), 7.81 (d, J=5 Hz, 1H), 9.02 (d, J=5 Hz, 1H), 9.37 (s, 1H) ppm.

Example No. 10

3-(N,N-Dimethylaminocarbamoyl)-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole (Table 1, No. 502)

Step 1: Ethyl 2-Amino-2-(4-trifluoromethyl-3-pyridinecarbonyloxyimino)acetate

17.3 g of carbonyldiimidazole are initially charged in 200 ml of 1,4-dioxane and, a little at a time, admixed with 20 g of 4-trifluoromethyl-3-pyridinecarboxylic acid. The mixture is stirred at room temperature for 1 h and subsequently heated to 45° C. for 2 h. After cooling to 30° C., 14.5 g of ethoxycarbonylformamide oxime are added and the mixture is stirred at 45° C. for 3 h. The precipitated solid is filtered off with suction and the filtrate is concentrated to 50 ml and, together with the solid, added to 250 ml of ice-water. The solid is filtered off with suction and dried at 50° C. under reduced pressure. This gives 28.7 g of the product as a white solid of mp. 172-174° C.

Step 2: 3-Ethoxycarbonyl-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

20 g of ethyl 2-amino-2-(4-trifluormethyl-3-pyridinecarbonyloxyimino)-acetate are dissolved in 200 ml of a mixture of xylene and toluene and admixed with 5 g of Amberlyst 15. The mixture is boiled at 125-130° C. for 6 h using a Dean-Stark apparatus. After the reaction has ended, the mixture is cooled and admixed with a small amount of diethyl ether. The mixture is filtered with suction through a glass filter frit, and the solution is then concentrated. This gives 15.8 g of the product as a yellow oil.

Step 3: 5-(4-Trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole-3-carboxylic Acid

15.8 g of 3-ethoxycarbonyl-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole are initially charged in 13 ml of methanol, and, with ice-cooling at 0° C., a solution of 2.8 g of lithium hydroxide in 50 ml of water is added dropwise. The mixture is stirred at room temperature for 2 h, 20 ml of ice-water are added and the mixture is extracted with 200 ml of diethyl ether. The aqueous phase is adjused to pH=2 using dil. HCl, and the precipitated product is filtered off with suction. After drying, 13.8 g of 5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole-3-carboxylic acid are obtained as a white solid of mp. 157-159° C.

Step 4: N,N-Dimethyl-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole-3-carboxamide

5.8 g of carbonyldiimidazole are initially charged in 90 ml of tetrahydrofuran and, a little at a time, admixed with 9 g of 5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole-3-carboxylic acid. The mixture is stirred at room temperature for 15 min and then heated at 50° C. for 2 h. After cooling to room temperature, 2.3 g of dimethylamine are introduced in a very gentle gas stream over a period of 2 h. After a reaction time of 12 h, the mixture is concentrated and taken up in 200 ml of diethyl ether. The mixture is washed with ice-cold half conc. hydrochloric acid solution, washed neutral with sat. sodium bicarbonate sol., dried over magnesium sulfate and concentrated under reduced pressure. This gives a slightly yellow oil which solidifies after a number of days to a solid of mp. 52-54° C.

In a similar manner, it is possible to prepare the compounds shown in Tables 1 to 6 below. The abbreviations used denote Ph: phenyl THP: 2-tetrahydropyranyl

TABLE 1

No. X Y m W R¹ m.p. [° C.] 1 N CCl₃ 0 O CH₃ 2 N CCl₃ 0 O CH₂CH₃ 3 N CCl₃ 0 O COOCH₂CH₃ 4 CH CCl₃ 0 O CH₃ 5 CH CCl₃ 0 O COOCH₂CH₃ 6 N (CF₂)₃CHCF₂ 0 O CH₃ 7 N (CF₂)₃CHCF₂ 0 O COOCH₂CH₃ 8 CH (CF₂)₃CHCF₂ 0 O CH₃ 9 CH (CF₂)₃CHCF₂ 0 O COOCH₂CH₃ 10 N (CF₂)₃CHCF₂ 0 S CH₂COOC(CH₃)₃ 11 N (CF₂)₃CHCF₂ 0 S CH₂CONHCH₃ 12 CH (CF₂)₃CHCF₂ 0 S (CH₂)₂CH₃ 13 CH (CF₂)₃CHCF₂ 0 S COOCH₂CH₃ 14 N (CF₂)₂CHCF₂ 0 O CH₂CH₃ 15 N (CF₂)₂CHCF₂ 0 O COOCH₂CH₃ 16 N (CF₂)₂CHCF₂ 0 O OH 17 N (CF₂)₂CHCF₂ 0 O OCH₃ 18 CH (CF₂)₂CHCF₂ 0 O CH₃ 19 CH (CF₂)₂CHCF₂ 0 O COOCH₂CH₃ 20 CH (CF₂)₂CHCF₂ 0 O OH 21 CH (CF₂)₂CHCF₂ 0 O NHCH₃ 22 N CF₂CF₃ 0 O CH₃ 23 N CF₂CF₃ 0 O CH₂CH₃ 24 N CF₂CF₃ 0 O (CH₂)₂CH₃ 25 N CF₂CF₃ 0 O CH(CH₃)₂ 26 N CF₂CF₃ 0 O Cyclo-C₆H₁₁ 27 N CF₂CF₃ 0 O CH₂C═CH₂ 28 N CF₂CF₃ 0 O CH₂C≡CH 29 N CF₂CF₃ 0 O CH₂CH₂C≡CH 30 N CF₂CF₃ 0 O CH₂C≡CCH₂CH₃ 31 N CF₂CF₃ 0 O (CH₂)₄C≡CH 32 N CF₂CF₃ 0 O CHFCF₃ 33 N CF₂CF₃ 0 O COOCH₂CH₃ 34 N CF₂CF₃ 0 O CH₂COOC(CH₃)₃ 35 N CF₂CF₃ 0 O CH₂CONHCH₃ 36 N CF₂CF₃ 0 O NH₂ 37 N CF₂CF₃ 0 O NHCH₂CH₃ 38 CH CF₂CF₃ 0 O CH₃ 39 CH CF₂CF₃ 0 O CH₂CH₃ 40 CH CF₂CF₃ 0 O (CH₂)₂CH₃ 41 CH CF₂CF₃ 0 O CH(CH₃)₂ 42 CH CF₂CF₃ 0 O Cyclo-C₆H₁₁ 43 CH CF₂CF₃ 0 O CH₂C═CH₂ 44 CH CF₂CF₃ 0 O CH₂COOC(CH₃)₃ 45 CH CF₂CF₃ 0 O NH₂ 46 CH CF₂CF₃ 0 O NHCOCH₃ 47 CH CF₂CF₃ 0 O NHCOCH₂CH₃ 48 N CF₂CF₃ 0 S CH₃ 49 N CF₂CF₃ 0 S CH₂CH₃ 50 N CF₂CF₃ 0 S (CH₂)₂CH₃ 51 N CF₂Cl 0 O CH₃ 52 N CF₂Cl 0 O CH₂CH₃ 53 N CF₂Cl 0 O (CH₂)₂CH₃ 54 N CF₂Cl 0 O CH(CH₃)₂ 55 N CF₂Cl 0 O CH₂COOC(CH₃)₃ 56 N CF₂Cl 0 O CH₂CONHCH₃ 57 N CF₂Cl 0 O OH 58 N CF₂Cl 0 O OCH₃ 59 N CF₂Cl 0 O OCH₂CH₃ 60 N CF₂Cl 0 O NHCH₃ 61 CH CF₂Cl 0 O CH₃ 62 CH CF₂Cl 0 O CH₂CH₃ 63 CH CF₂Cl 0 O (CH₂)₂CH₃ 64 CH CF₂Cl 0 O CH(CH₃)₂ 65 CH CF₂Cl 0 O CH₂COOC(CH₃)₃ 66 CH CF₂Cl 0 O CH₂CONHCH₃ 67 CH CF₂Cl 0 O OH 68 CH CF₂Cl 0 O OCH₃ 69 CH CF₂Cl 0 O OCH₂CH₃ 70 CH CF₂Cl 0 O NHCH₃ 71 CH CF₂Cl 0 O Cyclo-C₆H₁₁ 72 CH CF₂Cl 0 O CH₂C═CH₂ 73 CH CF₂Cl 0 O COOCH₂CH₃ 74 CH CF₂Cl 0 O CH₂COOC(CH₃)₃ 75 CH CF₂Cl 0 O CH₂CONHCH₃ 76 CH CF₂Cl 0 O OCH₃ 77 CH CF₂Cl 0 O NHCH₃ 78 CH CF₃ 0 O CH₃ oil 79 CH CF₃ 0 O CH₂CH₃ oil 80 CH CF₃ 0 O (CH₂)₂CH₃ oil 81 CH CF₃ 0 O CH(CH₃)₂ oil 82 CH CF₃ 0 O Cyclo-C₃H₅ oil 83 CH CF₃ 0 O (CH₂)₃CH₃ oil 84 CH CF₃ 0 O CH(CH₃)CH₂CH₃ oil 85 CH CF₃ 0 O CH₂CH(CH₃)₂ oil 86 CH CF₃ 0 O C(CH₃)₃ oil 87 CH CF₃ 0 O Cyclo-C₄H₇ 88 CH CF₃ 0 O (CH₂)₄CH₃ oil 89 CH CF₃ 0 O CH(CH₃)(CH₂)₂CH₃ 90 CH CF₃ 0 O (CH₂)₂CH(CH₃)₂ 91 CH CF₃ 0 O CH₂C(CH₃)₃ 92 CH CF₃ 0 O Cyclo-C₅H₉ oil 93 CH CF₃ 0 O (CH₂)₅CH₃ 94 CH CF₃ 0 O C(CH₂CH₃)₂CH₃ 95 CH CF₃ 0 O Cyclo-C₆H₁₁ 96 CH CF₃ 0 O (CH₂)₆CH₃ 97 CH CF₃ 0 O CH(CH₃)(CH₂)₄CH₃ 98 CH CF₃ 0 O Cyclo-C₇H₁₃ 99 CH CF₃ 0 O CH₂-cyclo-C₆H₁₁ 100 CH CF₃ 0 O 2-Norbornyl 101 CH CF₃ 0 O (CH₂)₇CH₃ 102 CH CF₃ 0 O CH(CH₂CH₃)(CH₂)₅CH₃ 103 CH CF₃ 0 O (CH₂)₈CH₃ 104 CH CF₃ 0 O (CH₂)₃-cyclo-C₆H₁₁ 105 CH CF₃ 0 O (CH₂)₉CH₃ 106 CH CF₃ 0 O 1-Adamantyl 107 CH CF₃ 0 O (CH₂)₁₀CH₃ 108 CH CF₃ 0 O (CH₂)₁₁CH₃ 109 CH CF₃ 0 O CH(CH₃)(CH₂)₉CH₃ 110 CH CF₃ 0 O (CH₂)₁₂CH₃ 111 CH CF₃ 0 O (CH₂)₁₃CH₃ 112 CH CF₃ 0 O (CH₂)₁₄CH₃ 113 CH CF₃ 0 O (CH₂)₁₅CH₃ 114 CH CF₃ 0 O (CH₂)₁₇CH₃ 115 CH CF₃ 0 O (CH₂)₁₉CH₃ 116 CH CF₃ 0 O CHO 117 CH CF₃ 0 O CH═CH₂ oil 118 CH CF₃ 0 O CH₂C═C(CH₃)₂ 119 CH CF₃ 0 O CH₂CH₂C═CH₂ 120 CH CF₃ 0 O CH₂C═CH₂ 121 CH CF₃ 0 O C(CH₃)═CH₂ 122 CH CF₃ 0 O (E)-CH₂CH═CHCH₂CH₃ 123 CH CF₃ 0 O (Z)-CH₂CH═CHCH₂CH₃ 124 CH CF₃ 0 O (CH₂)₅C═CH₂ 125 CH CF₃ 0 O C(═CHCH₃)CH₃ 62-64 126 CH CF₃ 0 O Geranyl 127 CH CF₃ 0 O 3-Menthyl 128 CH CF₃ 0 O C≡CH 129 CH CF₃ 0 O CH₂C≡CH 130 CH CF₃ 0 O CH₂CH₂C≡CH 131 CH CF₃ 0 O CH₂CH₂C≡CH 132 CH CF₃ 0 O (CH₂)₄C≡CH 133 CH CF₃ 0 O CHFCF₃ oil 134 CH CF₃ 0 O COOCH₂CH₃ oil 135 CH CF₃ 0 O CH₂CH₂OH oil 136 CH CF₃ 0 O CH₂CH₂OCH₃ oil 137 CH CF₃ 0 O CH₂COOC(CH₃)₃ oil 138 CH CF₃ 0 O CH₂SC₆H₅ oil 139 CH CF₃ 0 O CH₂CONHCH₃ 109-111 140 CH CF₃ 0 O CH₂CH(OH)CH₂OH 141 CH CF₃ 0 O CH₂COCH₃ 142 CH CF₃ 0 O COCH3 143 CH CF₃ 0 O CH₂OC₆H₅ 144 CH CF₃ 0 O COC₆H₅ 145 CH CF₃ 0 O CO(4-Cl)—C₆H₄ 146 CH CF₃ 0 O CF₂CH₃ 147 CH CF₃ 0 O CH₂CN 148 CH CF₃ 0 O CH₂CH₂CN 149 CH CF₃ 0 O CH₂CH(—O—)CH₂ 150 CH CF₃ 0 O CH₂(4-OCH₃)C₆H₅ 151 CH CF₃ 0 O CH₂-cyclo-(4-Oxo)-C₆H₈ 152 CH CF₃ 0 O CH₂CH(OH)CH₂SC₆H₅ 153 CH CF₃ 0 O CH₂CH₂Si(CH₃)₃ 154 CH CF₃ 0 O CH═CF₂ 155 CH CF₃ 0 O CCl═CHCl 156 CH CF₃ 0 O 2-Pyridyl  99-101 157 CH CF₃ 0 O 2-Furyl 158 CH CF₃ 0 O 2-Thienyl 106-108 159 CH CF₃ 0 O CH₂C≡CCH₂CH₂OTHP 160 CH CF₃ 0 O CH₂CH₂CI oil 161 CH CF₃ 0 O Si(CH₃)₃ 162 CH CF₃ 0 O OC₆H₅ 163 CH CF₃ 0 O OH 164 CH CF₃ 0 O OCH₃ 165 CH CF₃ 0 O OCH₂CH₃ 166 CH CF₃ 0 O OCHF₂ 167 CH CF₃ 0 O OCH₂C₆H₅ 168 CH CF₃ 0 O CH₂SCH₃ 48-49 169 CH CF₃ 0 O SC₆H₅ 170 CH CF₃ 0 O SeC₆H₅ 171 CH CF₃ 0 O NH₂ 116-118 172 CH CF₃ 0 O NHCH₃ 173 CH CF₃ 0 O NHCH₂CH₃ 174 CH CF₃ 0 O N(CH₂CH₃)₂ 175 CH CF₃ 0 O CONHCH₂C═CH₂ 105-107 176 CH CF₃ 0 O Cl 177 CH CF₃ 0 O Br 178 CH CF₃ 0 O CONH₂ 206-208 179 CH CF₃ 0 O NHCOCH₃ 129-131 180 CH CF₃ 0 O NHCOCH₂CH₃ 181 CH CF₃ 0 O OSO₂CH₃ 182 CH CF₃ 0 O SOCH₂(4-Br)—C₆H₄ 183 CH CF₃ 0 O N(CH₃)COOCH₂C₆H₅ 184 CH CF₃ 0 O NHNH₂ 185 CH CF₃ 0 O NHN(CH₃)₂ 186 N CF₃ 0 O CH₃ 187 N CF₃ 0 O CH₂CH₃ oil 188 N CF₃ 0 O (CH₂)₂CH₃ oil 189 N CF₃ 0 O CH(CH₃)₂ oil 190 N CF₃ 0 O (CH₂)₃CH₃ oil 191 N CF₃ 0 O CH₂CH(CH₃)₂ oil 192 N CF₃ 0 O C(CH₃)₃ 193 N CF₃ 0 O (CH₂)₄CH₃ oil 194 N CF₃ 0 O CH(CH₃)(CH₂)₂CH₃ 195 N CF₃ 0 O CH₂C(CH₃)₃ 196 N CF₃ 0 O Cyclo-C₅H₉ 197 N CF₃ 0 O (CH₂)₅CH₃ 198 N CF₃ 0 O Cyclo-C₆H₁₁ 199 N CF₃ 0 O CH(CH₃)(CH₂)₄CH₃ 200 N CF₃ 0 O CH₂-cyclo-C₆H₁₁ 201 N CF₃ 0 O (CH₂)₇CH₃ 202 N CF₃ 0 O (CH₂)₈CH₃ 203 N CF₃ 0 O (CH₂)₉CH₃ 204 N CF₃ 0 O CH(CH₃)(CH₂)₉CH₃ 205 N CF₃ 0 O (CH₂)₁₅CH₃ 206 N CF₃ 0 O (CH₂)₁₇CH₃ 207 N CF₃ 0 O (CH₂)₁₉CH₃ 208 N CF₃ 0 O CH₂CH═C(CH₃)₂ 209 N CF₃ 0 O CH₂CH₂CH═CH₂ 210 N CF₃ 0 O CH₂CH═CH₂ 211 N CF₃ 0 O (Z)-CH₂CH═CHCH₂CH₃ 212 N CF₃ 0 O (CH₂)₅CH═CH₂ 213 N CF₃ 0 O CH₂C≡CH 214 N CF₃ 0 O CH₂C≡CCH₂CH₃ 215 N CF₃ 0 O CHFCF₃ 216 N CF₃ 0 O COOCH₂CH₃ 217 N CF₃ 0 O CH₂CH₂OH 218 N CF₃ 0 O CH₂CH₂OCH₃ 219 N CF₃ 0 O CH₂COOC(CH₃)₃ 220 N CF₃ 0 O CH₂SC₆H₅ 221 N CF₃ 0 O CH₂CONHCH₃ 222 N CF₃ 0 O CH₂CH(OH)CH₂OH 223 N CF₃ 0 O CHO 224 N CF₃ 0 O COCH₃ 225 N CF₃ 0 O CH₂OC₆H₅ 226 N CF₃ 0 O COC₆H₅ 227 N CF₃ 0 O CF₂CH₃ 228 N CF₃ 0 O CH₂CN 229 N CF₃ 0 O CH₂CH₂CN 230 N CF₃ 0 O CH═CF₂ 231 N CF₃ 0 O 2-Furyl 232 N CF₃ 0 O CH₂C≡C—I 233 N CF₃ 0 O OH 234 N CF₃ 0 O OCH₃ 235 N CF₃ 0 O OCH₂CH₃ 236 N CF₃ 0 O OCHF₂ 237 N CF₃ 0 O OCH₂C₆H₅ 238 N CF₃ 0 O SC₆H₅ 239 N CF₃ 0 O NH₂ 240 N CF₃ 0 O NHCH₃ 241 N CF₃ 0 O NHCH₂CH₃ 242 N CF₃ 0 O N(CH₂CH₃)₂ 243 N CF₃ 0 O N(CH₂CN)₂ 244 N CF₃ 0 O N(CH₃)₂ 245 N CF₃ 0 O NHCOCH₃ 246 N CF₃ 0 O NHCOCH₂CH₃ 247 N CF₃ 0 O OSO₂CH₃ 248 N CF₃ 0 O NHNH₂ 249 CH CF₃ 0 S CH₃ 250 CH CF₃ 0 S CH₂CH₃ 251 CH CF₃ 0 S (CH₂)₂CH₃ 252 CH CF₃ 0 S CHO 253 CH CF₃ 0 S CHFCF₃ 254 CH CF₃ 0 S CH₂C≡CH 255 CH CF₃ 0 S COOCH₂CH₃ 256 CH CF₃ 0 S CH₂COOC(CH₃)₃ 257 CH CF₃ 0 S CH₂CN 258 CH CF₃ 0 S SeC₆H₅ 259 N CF₃ 0 S CH₃ 260 N CF₃ 0 S CH₂CH₃ 261 N CF₃ 0 S (CH₂)₂CH₃ 262 N CF₃ 0 S CHFCF₃ 263 N CF₃ 0 S CH₂CH₂OH 264 N CF₃ 0 S CH₂COOC(CH₃)₃ 265 CH CH₂CH₂Cl 0 O CH₃ 266 CH CH₂CH₂Cl 0 O CH₂CH₃ 267 CH CH₂CH₂Cl 0 O (CH₂)₂CH₃ 268 CH CH₂CH₂Cl 0 O CH(CH₃)₂ 269 CH CH₂CH₂Cl 0 O CH₂SC₆H₅ 270 CH CH₂CH₂Cl 0 O CH₂CONHCH₃ 271 CH CH₂CH₂Cl 0 O NH₂ 272 CH CH₂CH₂Cl 0 O NHCH₂CH₃ 273 N CH₂CH₂Cl 0 O CH₂CH₃ 274 N CH₂CH₂Cl 0 O NH₂ 275 N CH₂Cl 0 O CH₃ 276 CH CH₂Cl 0 O CH₃ 277 CH CHF₂ 0 O CH₃ 278 CH CHF₂ 0 O CH₂CH₃ 279 CH CHF₂ 0 O (CH₂)₂CH₃ 280 CH CHF₂ 0 O CH₂CH═CH₂ 281 CH CHF₂ 0 O C(CH₃)═CH₂ 282 CH CHF₂ 0 O COOCH₂CH₃ 283 CH CHF₂ 0 O CH₂CONHCH₃ 284 CH CHF₂ 0 O CF₂CH₃ 285 CH CHF₂ 0 O CHO 286 CH CHF₂ 0 O NH₂ 287 CH CHF₂ 0 O Cl 288 CH CHF₂ 0 O NHCOCH₃ 289 CH CHF₂ 0 O NHNH₂ 290 N CHF₂ 0 O CH₃ 291 N CHF₂ 0 O CH₂CH₃ 292 N CHF₂ 0 O CH(CH₃)(CH₂)₄CH₃ 293 N CHF₂ 0 O CH₂CH═CH₂ 294 N CHF₂ 0 O COOCH₂CH₃ 295 N CHF₂ 0 O NH₂ 296 CH CF₃ 1 O CH₃ 297 CH CF₃ 1 O COOCH₂CH₃ 298 CH CF₃ 1 O CH₂COOC(CH₃)₃ 299 CH CF₃ 1 O CHFCF₃ 300 N CF₃ 0 O CH₂NHSO₂CH₃ 301 N CF₃ 0 O (CH₂)₂NHSO₂CH₃ 302 N CF₃ 0 O CH₂NHSO₂CH₂CH₃ 303 N CF₃ 0 O CH₂NHSO₂CH₂C₆H₅ 304 CH CF₃ 0 O (CH₂)₄NHSO₂CF₃ 305 CH CF₃ 0 O (CH₂)₂S(CH₂)₂CH₃ 306 CH CF₃ 0 O (CH₂)₄S(CH₂)₄OCH₃ 307 CH CF₃ 0 S (CH₂)₂S(CH₂)₂CN 308 CH CF₃ 0 S CH₂NHSO₂CH₂CH₃ 309 CH CF₃ 0 S CH₂NHSO₂CH₂C₆H₅ 310 CH CF₃ 0 S (CH₂)₂NHSO₂CH₃ 311 CH CF₃ 0 S CH₂NHSO₂CH₃ 312 CH CF₃ 0 S CH(CH₃)CH₂NHC₆H₅ 313 CH CF₃ 0 S (CH₂)₂S(2-F)—C₆H₄ 314 CH CF₃ 0 S (CH₂)₆NHCH₂)₆OCH₃ 315 CH CF₃ 0 S (CH₂)₂NH—(2-F)—C₆H₄ 316 CH CF₃ 0 S (CH₂)₃NHCH₂CN 317 CH CF₃ 0 S (CH₂)₂O(3-Cl)—C₆H₄ 318 CH CF₃ 0 S (CH₂)₆NHCH₂CF₃ 319 CH CF₃ 0 S (CH₂)₂O(3-CH₃)—C₆H₄ 320 CH CF₃ 0 O CH₂NHC₆H₅ 321 CH CF₃ 0 O (CH₂)₄S(2-Br)—C₆H₄ 322 CH CF₃ 0 O (CH₂)₆NH(CH₂)₂OCH₃ 323 CH CF₃ 0 O (CH₂)₂NH(CH₂)₄OCH₃ 324 CH CF₃ 0 O (CH₂)₃NH—(4-CN)—C₆H₄ 325 CH CF₃ 0 O (CH₂)₂O(3-CH₃)—C₆H₄ 326 CH CF₃ 0 O (CH₂)₄NHCH₂CF₃ 327 CH CF₃ 0 O (CH₂)₄NHCH₂CN 328 CH CF₃ 0 O (CH₂)₃O(4-OCH₃)—C₆H₄ 329 CH CF₃ 0 O CH₂SO₂-tert-C₄H₉ oil 330 CH CF₃ 0 O CH₂SO₂—(4-F)—C₆H₄ oil 331 CH CF₃ 0 O CH₂SO₂—C₆H₅ oil 332 CH CF₃ 0 O CH₂SOCH₃  63 333 CH CF₃ 0 O CH₂SO—C₆H₅ oil 334 CH CF₃ 0 O CH₂CONH(CH₂)₂CH₃ 80-82 335 CH CF₃ 0 O (4-OCF₃)—C₆H₄ 57-59 336 CH CF₃ 0 O CH₂OCH₃ oil 337 CH CF₃ 0 O

53-54 338 CH CF₃ 0 O

oil 339 CH CF₃ 0 O CH₂CH₂OCH₂CH₃ oil 340 CH CF₃ 0 O CH₂CH₂NC₆H₅ 80-83 341 CH CF₃ 0 O

80-81 342 CH CF₃ 0 O

110-111 343 CH CF₃ 0 O CH₂CH₂O(CO)—(4-Cl)—C₆H₄ 80-82 344 CH CF₃ 0 O CH₂—(4-OCH₃)—C₆H₄ 54-55 345 CH CF₃ 0 O CH₂—(3-Cl)—C₆H₄ 51-52 346 CH CF₃ 0 O CH₂-cyclo-C₃H₅ oil 347 CH CF₃ 0 O CH₂—(4-C₆H₅)—C₆H₄ oil 348 CH CF₃ 0 O

143-144 349 CH CF₃ 0 O CH₂CH₂O(CO)—(2,6-F₂)—C₆H₃ 57-58 350 CH CF₃ 0 O CH₂CH₂O(CO)—(4-NO₂)—C₆H₄ 80-81 351 CH CF₃ 0 O CH₂—(2,6-Cl₂)—C₆H₃ 91-92 352 CH CF₃ 0 O CH₂CH₂OSO₂CH₃ oil 353 CH CF₃ 0 O CH₂CH₂O(CO)-tert-C₄H₉ oil 354 CH CF₃ 0 O CH₂—(3-F)—C₆H₄ 50-51 355 CH CF₃ 0 O CH₂CONCH₂C≡CH 129-131 356 CH CF₃ 0 O CH₂CH₂O(CO)-cyclo-C₃H₇ oil 357 CH CF₃ 0 O CH₂CH₂O(CO)CH₃ oil 358 CH CF₃ 0 O CH₂—[2,4-(CH₃)₂]—C₆H₃ 85-86 359 CH CF₃ 0 O CH₂CONCH₂CH═CH₂ 210-212 360 CH CF₃ 0 O CH₂CON(CH₂CH₃)₂ oil 361 CH CF₃ 0 O CH₂CON(CH₂)₃CH₃ 77-79 362 CH CF₃ 0 O CH₂CONCH₂-(2-furyl) 139-141 363 CH CF₃ 0 O CH₂CONCH(CH₃)₂ 112-114 364 CH CF₃ 0 O CH₂CONCH(CH₃)[(CH₂)₄CH₃] 73-75 365 CH CF₃ 0 O CH₂CONCH₂CH₂C₆H₅ 120-122 366 CH CF₃ 0 O CH₂CONCH₂CH₂OCH₂CH₃  78 367 CH CF₃ 0 O CH₂CONCH₂CF₃ 176-178 368 CH CF₃ 0 O CH₂CONCH(CH₃)[(CH₂)₅CH₃] 85-86 369 CH CF₃ 0 O

oil 370 CH CF₃ 0 O

oil 371 CH CF₃ 0 O CH₂CH2-(1-pyrryl) oil 372 CH CF₃ 0 O CH₂CH₂C₆H₅ oil 373 CH CF₃ 0 O CH₂Cl 53-54 374 CH CF₃ 0 O (CH₂)₃OH 38-39 375 CH CF₃ 0 O CH₂CONCH(CH₃)[(CH₂)₂]CH₃ 68-69 376 CH CF₃ 0 O CH₂CH(OCH₃)₂ oil 377 CH CF₃ 0 O CH₂CONCH₂C(CH₃)₃ oil 378 CH CF₃ 0 O CH₂CONC(CH₃)₂(CH₂CH₃) oil 379 CH CF₃ 0 O CH₂CONCH₂CH₂-cyclo-C₆H₁₁ 82-85 380 CH CF₃ 0 O CH₂CONCH(CH₃)(1-naphthyl) 142-146 381 CH CF₃ 0 O (CH₂)₃Cl oil 382 CH CF₃ 0 O CH₂CON-tert-C₄H₉ oil 383 CH CF₃ 0 O CH₂CON(iso-C₃H₇)₂ 70-72 384 CH CF₃ 0 O CH₂CON(CH₂)₇CH₃ 79-81 385 CH CF₃ 0 O CH₂CON-cyclo-C₆H₁₁ 119-121 386 CH CF₃ 0 O CH₂CONCH₂CH₂—(4-Cl)—C₆H₄ 120-121 387 CH CF₃ 0 O CH₂CONCH₂-(2-thienyl) 137-139 388 CH CF₃ 0 O

151-153 389 CH CF₃ 0 O CH₂CONHCH(CH₃)(CH₂CH₃) 87-89 390 CH CF₃ 0 O (CH₂)₃SCH₃ oil 391 CH CF₃ 0 O (CH₂)₃SOCH₃ oil 392 CH CF₃ 0 O CH₂CONC(CH₃)₂(C≡CH) 111-113 393 CH CF₃ 0 O CH₂CONCH(CH₃)CH₂CH₂CH(CH₃)₂ 72-74 394 CH CF₃ 0 O

oil 395 CH CF₃ 0 O CH₂CON-cyclo-C₅H₉ 110-112 396 CH CF₃ 0 O CH₂CON(CH₂)₄CH₃ 75-77 397 CH CF₃ 0 O

190-192 398 CH CF₃ 0 O CH₂CON(3-CF₃)C₆H₄ 136-138 399 CH CF₃ 0 O CH₂CON-cyclo-C₈H₁₇ 115-117 400 CH CF₃ 0 O

oil 401 CH CF₃ 0 O CH₂CON-Adamantyl oil 402 CH CF₃ 0 O CH₂CON(CH₂CH₂CH₃)₂ oil 403 CH CF₃ 0 O CH₂CONCH(CH₃)[(4-F)—C₆H₄] 111-113 404 CH CF₃ 0 O CH₂CONCH₂CH(CH₃)₂ 91-93 405 CH CF₃ 0 O

Oil 406 CH CF₃ 0 O CH₂CONCH₂CH₂OC₆H₅  99-101 407 CH CF₃ 0 O CH₂CH═NOCH₃ oil 408 CH CF₃ 0 O CH₂CONCH₂CH₂—[3,4-(OCH₃)₂]C₆H₃ 123-125 409 CH CF₃ 0 O CH₂CON—(2-Cl)C₆H₄ 138-140 410 CH CF₃ 0 O CH₂CON—(2-SCH₃)C₆H₄ 136-138 411 CH CF₃ 0 O

222-225 412 CH CF₃ 0 O

207-209 413 CH CF₃ 0 O CH₂CON—(3-Br)C₆H₄ 129-131 414 CH CF₃ 0 O CH₂CON—N—(2,4,6-Cl₃)C₆H₂ 153-155 415 CH CF₃ 0 O CH₂CON—(4-I)C₆H₄ 143-145 416 CH CF₃ 0 O CH₂CON—NCOCH₂(3-Thienyl) 185-187 417 CH CF₃ 0 O CH₂CH₂CHO oil 418 CH CF₃ 0 O CH₂CON(CH₃)[(CH₂)₃CH₃] oil 419 CH CF₃ 0 O CH₂CON—(3,5-Cl₂-2,4-F₂)C₆H 166-167 420 CH CF₃ 0 O CH₂CON—C₆H₅ 215-217 421 CH CF₃ 0 O CH₂CON(CH₃)(C₆H₁₁) oil 422 CH CF₃ 0 O CH₂CON(CH₂CH₃)(CH₂CH═CH₂) oil 423 CH CF₃ 0 O CH₂CON(CH₂CH₃)[CH(CH₃)₂] oil 424 CH CF₃ 0 O CH₂CONCH(CH₃)[(CH₃)₂] 108-110 425 CH CF₃ 0 O CH₂CON(CH₂CH₃)[CH₂C(═CH₂)(CH₃)] oil 426 CH CF₃ 0 O CH₂CONCH₂(4-tert-C₄H₉)C₆H₄ oil 427 CH CF₃ 0 O CH₂CONCH(CH₃)(tert-C₄H₉) oil 428 CH CF₃ 0 O CH₂CONCH(CH₃)[CH₂CH(CH₃)(CH₂CH₃)] oil 429 CH CF₃ 0 O CH₂CONCH₂COOCH₂CH₃ 103-105 430 CH CF₃ 0 O CH₂CON[(CH₂)₂CH₃](CH₂-cyclo-C₃H₇) oil 431 CH CF₃ 0 O CH₂CONCH(CH₃)CH₂CH₂CH(CH₃)₂ 80-82 432 CH CF₃ 0 O CH₂CONCH(CH₂CH₃)[CH₂CH(CH₃)₂] oil 433 CH CF₃ 0 O CH₂C═O-(1-Piperidinyl) oil 434 CH CF₃ 0 O

180-182 435 CH CF₃ 0 O CH₂CONCH₂C(═CH2)(CH₃) 86-87 436 CH CF₃ 0 O CH₂CONCH[CH(CH₃)₂](COOCH₃) oil 437 CH CF₃ 0 O CH₂CONCH₂-cyclo-C₃H₇ oil 438 CH CF₃ 0 O CH₂CON(CH₂)₅OH oil 439 CH CF₃ 0 O CH₂CON(CH₃)(CH₂CO₂CH₃) oil 440 CH CF₃ 0 O CH₂CON(CH₃)(CH₂CN) oil 441 CH CF₃ 0 O CH₂CONCH[CH₂CH(CH₃)₂](CO₂CH₃) oil 442 CH CF₃ 0 O CH₂CON-(1-Piperidinyl) oil 443 CH CF₃ 0 O CH₂CONCH₂CH₂OCH₃ 97-99 444 CH CF₃ 0 O CH₂CH₂SC₆H₅ oil 445 CH CF₃ 0 O CH₂CH₂SCH₃ oil 446 CH CF₃ 0 O CH₂CH₂SCH₂C₆H₅ oil 447 CH CF₃ 0 O

oil 448 CH CF₃ 0 O CH₂CON—(2-OH)C₆H₄ 162-164 449 CH CF₃ 0 O CH₂CON—(3-OH)C₆H₄ oil 450 CH CF₃ 0 O CH₂CON—(2-CH₃)C₆H₄ 163-164 451 CH CF₃ 0 O CH₂CON—(3-NO₂)C₆H₄ 176-178 452 CH CF₃ 0 O CH₂CON—(3-OCF₂CHFCl)C₆H₄ 120-121 453 CH CF₃ 0 O CH₂CON—(3-CF₃-4-F)C₆H₃ 168-170 454 CH CF₃ 0 O CH₂CON—(2,4-Cl₂)C₆H₃ 120-122 455 CH CF₃ 0 O CH₂CON—(2-F-4.Cl)C₆H₃ 148-151 456 CH CF₃ 0 O CH₂CON—[2,4-(CH₃)₂]C₆H₃ 123-125 457 CH CF₃ 0 O CH₂CON—[2,3-(CH₃)₂]C₆H₃ waxy 458 CH CF₃ 0 O

waxy 459 CH CF₃ 0 O CH₂CON—(2-CH₃-3-Cl)C₆H₃ 160-162 460 CH CF₃ 0 O CH₂CON(CH₂CH₃)(C₆H₅) oil 461 CH CF₃ 0 O

124-126 462 CH CF₃ 0 O CH₂CON(2-OCH₃-5-Ph)C₆H₃ 167-169 463 CH CF₃ 0 O

157-158 464 CH CF₃ 0 O CH₂CON—(3-NO₂-4-Cl)C₆H₃ oil 465 CH CF₃ 0 O CH₂CON—(2-Cl-4-CH₃)C₆H₃ 106-108 466 CH CF₃ 0 O CH₂CON—(3-OCH₂CH₃)C₆H₄ waxy 467 CH CF₃ 0 O

169-171 468 CH CF₃ 0 O CH₂CON—(4-CH₃)C₆H₄ 139-141 469 CH CF₃ 0 O CH₂CON-(1-Naphthyl) 155-157 470 CH CF₃ 0 O CH₂CON—(3-I)C₆H₄ 135-137 471 CH CF₃ 0 O CH₂CON—(2-OCH₂CH₃)C₆H₄ 138 472 CH CF₃ 0 O CH₂CON—(2-OCH₃)C₆H₄ 130-132 473 CH CF₃ 0 O CH₂CON—[3,5-(OCH₃)₂]C₆H₃ 130-132 474 CH CF₃ 0 O CH₂CON—(4-Cl)C₆H₄ 139-141 475 CH CF₃ 0 O CH₂CON—(3-CH₃)C₆H₄ oil 476 CH CF₃ 0 O CH₂CON—(3-OCH₃)C₆H₄ oil 477 CH CF₃ 0 O CH₂CON—(4-CH₂CH₃)C₆H₄ 122-123 478 CH CF₃ 0 O CH₂CON—(4-CF₃)C₆H₄ 151-152 479 CH CF₃ 0 O CH₂CON—(2-CH₃-4-Cl)C₆H₃ 165-167 480 CH CF₃ 0 O CH₂CH₂NCH₂C₆H₅ oil 481 CH CF₃ 0 O CH₂CH₂NCH₂-(3-Pyridyl) oil 482 CH CF₃ 0 O CH₂CH═NOCH₂CH₃ oil 483 CH CF₃ 0 O CH₂CH═NOC₆H₅ oil 484 CH CF₃ 0 O CH₂CON—(4-NO₂)C₆H₄ 181-183 485 CH CF₃ 0 O CH₂CON—(2-CH₃-4-NO₂)C₆H₃ 129-131 486 CH CF₃ 0 O CH₂CON—(2-Cl-3-CF₃)C₆H₃ 136 487 CH CF₃ 0 O CH₂CON—(2-CN-4-Cl)C₆H₃ 157-159 488 CH CF₃ 0 O CH₂CON—(3,5-Cl₂)C₆H₃ 167-169 489 CH CF₃ 0 O CH₂CON—(3,5-Cl₂-4-OCF₂CHF₂)C₆H₂ 132-134 490 CH CF₃ 0 O CH₂CON—(2,4,5-Cl₃)C₆H₂ 146 491 CH CF₃ 0 O CH₂CON—(3,5-Cl₂-4-OCF₂CHFCF₃)C₆H₂ 124-126 492 CH CF₃ 0 O CH₂CON—(2-CF₃-4-Cl)C₆H₃ 136 493 CH CF₃ 0 O

oil 494 CH CF₃ 0 O

91-93 495 CH CF₃ 0 O

123-125 496 CH CF₃ 0 O

81-83 497 CH CF₃ 0 O

113-115 498 CH CF₃ 0 O COOH 155-157 499 CH CF₃ 0 O 4-F—C₆H₄ 104-106 500 CH CF₃ 0 O CON(C₂H₅)₂ oil 501 CH CF₃ 0 O CONCH(CH₃)₂ oil 502 CH CF₃ 0 O CON(CH₃)₂ 52-54 503 CH CF₃ 0 O CONHCH₂CCH 105-107 504 CH CF₃ 0 O CONH-cyclo-C₃H₅ 101-103 505 CH CF₃ 0 O CONH₂ 206-208 506 CH CF₃ 0 O

72-74 507 CH CF₃ 0 O

 98-100 508 CH CF₃ 0 O

108-110 509 CH CF₃ 0 O

140-142 510 CH CF₃ 0 O CONHCH₃ 127-129 511 CH CF₃ 0 O CONHCH₂CH═CH₂ oil 512 CH CF₃ 0 O CON(CH₂CN)₂ 90-92 513 CH CF₃ 0 O 4-(t-C₄H₉)—C₆H₄ 64-66 514 CH CF₃ 0 O 4-CF₃-C₆H₄ 89-91 515 CH CF₃ 0 O 4-CH₃-3-F—C₆H₃ 104-106 516 CH CF₃ 0 O 2,4-di-Cl—C₆H₃ 70-72 517 CH CF₃ 0 O 4-(NHSO₂CH₃)—C₆H₄ 204-206 518 CH CF₃ 0 O 2,6-di-Cl—C₆H₃ 139-141 519 CH CF₃ 0 O COOCH₂C₆H₅ 83-85 520 CH CF₃ 0 O CONHC₃H₇ oil 521 CH CF₃ 0 O 3,5-di-Br-4-(OCH₃)—C₆H₂ 132-134 522 CH CF₃ 0 O CHCl₂ oil 523 CH CF₃ 0 O CCl₃ oil 524 CH CF₃ 0 O CH(OCH3)₂ oil 525 CH CF₃ 0 O 3-CF₃—C₆H₄ 57-59 526 CH CF₃ 0 O CON(CH₂)₅ oil 527 CH CF₃ 0 O CON(CH₃)CH₂C₆H₅ oil 528 CH CF₃ 0 O CONHCH₂C₆H₅ 96-98 529 CH CF₃ 0 O

oil 530 CH CF₃ 0 O CONH-n-C₆H₁₃ oil 531 CH CF₃ 0 O CON(CH₂CH₃)CH₂C₆H₅ oil 532 CH CF₃ 0 O CONH-c-C₆H₁₁ 115-117 533 CH CF₃ 0 O CON(n-C₄H₉)₂ oil 534 CH CF₃ 0 O

oil 535 CH CF₃ 0 O CONH-i-C₄H₉ oil 536 CH CF₃ 0 O

oil 537 CH CF₃ 0 O CON(CH₂)₄ 68-70 538 CH CF₃ 0 O CON(CH₃)-n-C₆H₁₃ oil 539 CH CF₃ 0 O

oil 540 CH CF₃ 0 O CON(CH₃)CH₂CH₃ oil 541 CH CF₃ 0 O CONHOCH₃ oil 542 CH CF₃ 0 O

oil 543 CH CF₃ 0 O CON(CH₃)CH₂CH₂CH₃ oil 544 CH CF₃ 0 O CONHCH₂CH(OCH₃)₂ oil 545 CH CF₃ 0 O CONH-t-C₄H₉ 113-115 546 CH CF₃ 0 O CONHCH₂-4-Cl—C₆H₄ oil 547 CH CF₃ 0 O CONHCH(CH₃)C₆H₅ oil 548 CH CF₃ 0 O CONHCH₂CH₂OCH₃ 92-94 549 CH CF₃ 0 O

190-192 550 CH CF₃ 0 O CONHC(CH₃)₂CCH 90-92 551 CH CF₃ 0 O CONHCH₂-2-Furyl 93-95 552 CH CF₃ 0 O CON(CH₂)₃ 91-93 553 CH CF₃ 0 O CONHCH₂-c-C₃H₅ oil 554 CH CF₃ 0 O CONHC(CH₃)₂CH₂CH₃ oil 555 CH CF₃ 0 O CONH(CH₂)₃C₆H₅ oil 556 CH CF₃ 0 O CONHCH₂-3-Pyridyl 132-134 557 CH CF₃ 0 O CON(CH₃)-n-C₄H₉ oil 558 CH CF₃ 0 O CON(CH₂CH3)-i-C₃H₇ oil 559 CH CF₃ 0 O

oil 560 CH CF₃ 0 O CONHCH₂CH₂Cl oil 561 CH CF₃ 0 O CONHCH₂CN 152-157 562 CH CF₃ 0 O CON(CH₃)OCH₃ oil 563 CH CF₃ 0 O CON(CH₃)CH₂CH═CH₂ oil 564 CH CF₃ 0 O CONHCH₂COOCH₃ oil 565 CH CF₃ 0 O CON(CH₃)-i-C₃H₇ oil 566 CH CF₃ 0 O CON(CH₃)CH₂CH₂CN oil 567 CH CF₃ 0 O CON(CH₃)CH₂CH(OCH₃)₂ oil 568 CH CF₃ 0 O CON(CH₃)CH₂CH(—CH₂CH₂O—) oil 569 CH CF₃ 0 O CONHCH₂C(═CH₂)CHH₃ oil 570 CH CF₃ 0 O CON(CH₂CH₃)CH₂CH═CH₂ oil 571 CH CF₃ 0 O CONHC₆H₅ 83-85 572 CH CF₃ 0 O CON(CH₃)CH₂CCH oil 573 CH CF₃ 0 O CON(CH₃)CH₂CN oil 574 CH CF₃ 0 O CON(CH₃)CH₂CH₂N(CH₃)₂ oil 575 CH CF₃ 0 O CONHOCH₂CH₃ 114-116 576 CH CF₃ 0 O CONHCH₂CF₃ 74-76 577 CH CF₃ 0 O CON(CH₂CH₂Cl)₂ oil 578 CH CF₃ 0 O CONH-c-C₄H₇ oil 579 CH CF₃ 0 O CON(CH₂CH₂CH₃)CH₂-c-C₃H₅ oil 580 CH CF₃ 0 O CON(CH₃)-c-C₆H₁₁ oil 581 CH CF₃ 0 O CON(CH₂CH₃)CH₂C(═CH₂)CH₃ oil 582 CH CF₃ 0 O CONHOCH₂CH═CH₂ 90-92 583 CH CF₃ 0 O CONHOCH₂C₆H₅ 126-128 584 CH CF₃ 0 O CON(CH₃)CH₂COOCH₃ oil 585 CH CF₃ 0 O COONHCH₃ 230-232 586 CH CF₃ 0 O CONHCH₂CH₃ 83-85 587 CH CF₃ 0 O CONHCH(CH₃)COOCH₃ 104-106 588 CH CF₃ 0 O CONHCH(i-C₃H₇)COOCH₃ oil 589 CH CF₃ 0 O CON(CH₃)CH₂CON(CH₃)₂ oil 590 CH CF₃ 0 O CON(CH₃)-t-C₄H₉ oil 591 CH CF₃ 0 O CONHO-t-C₄H₉ 103-105 592 CH CF₃ 0 O CON(CH₃)CH(i-C₃H₇)COOCH₃ oil 593 CH CF₃ 0 O CH(OCH₂CH₃)₂ oil 594 CH CF₃ 0 O

oil 595 CH CF₃ 0 O

oil 596 CH CF₃ 0 O

oil 597 CH CF₃ 0 O

oil 598 CH CF₃ 0 O

oil 599 CH CF₃ 0 O CONHCH₂CONHCH₃ 101-103 600 CH CF₃ 0 O CON(CH₂)₇ oil 601 CH CF₃ 0 O CON(CH₂)₆ oil 602 CH CF₃ 0 O CON(CH₂CH₃)CH₂CH₂OCH₃ oil 603 CH CF₃ 0 O

oil 604 CH CF₃ 0 O

oil 605 CH CF₃ 0 O

oil 606 CH CF₃ 0 O CON(CH₂CH₃)CH₂CH₂CN oil 607 CH CF₃ 0 O

oil 608 CH CF₃ 0 O CON(CH₂CH₃)-n-C₄H₉ oil 609 CH CF₃ 0 O

179-181 610 CH CF₃ 0 O CONHCH(CH₃)CONHCH₃ 136-138 611 CH CF₃ 0 O COON(CH₂)₄ 64-66 612 CH CF₃ 0 O CONHCH₂CON(CH₃)₂ 107-109 613 CH CF₃ 0 O CON(CH₂COOCH₂CH₃)₂ oil 614 CH CF₃ 0 O

180-182 615 CH CF₃ 0 O

221-223 616 CH CF₃ 0 O

234-236 617 CH CF₃ 0 O

oil 618 CH CF₃ 0 O CON(CH₃)CH₂-6-Cl-3-pyridyl oil 619 CH CF₃ 0 O

105-107 620 CH CF₃ 0 O CONHCH(CH₃)CH(OCH₃)₂ oil 621 CH CF₃ 0 O CONHCH₂CH₂SCH₃ oil 622 CH CF₃ 0 O CONHCH(CH₃)CH₂OCH₃ 70-72 623 CH CF₃ 0 O CONHCH₂CH₂NHCOCH₃ 124-126 624 CH CF₃ 0 O CONH(CH₂)₃OCH₂CH₃ oil 625 CH CF₃ 0 O CON(CH₂CH₃)CH₂CH₂CH₃ oil 626 CH CF₃ 0 O CON(CH₂CH₃)CH₂OCH₃ oil 627 CH CF₃ 0 O CONHCH₂CH₂SCH₂CH₃ oil 628 CH CF₃ 0 O CONHCH₂CH₂OCH₂CH₃ 59-61 629 CH CF₃ 0 O

oil 630 CH CF₃ 0 O

174-176 631 CH CF₃ 0 O CONHCH(CH₃)CH(OCH₃)₂ oil 632 CH CF₃ 0 O CONHCH₂CH₂SCH₃ oil 633 CH CF₃ 0 O CONHCH(CH₃)CH₂OCH₃ 70-72 634 CH CF₃ 0 O CONHCH₂CH₂NHCOCH₃ 124-126 635 CH CF₃ 0 O CONH(CH₂)₃OCH₂CH₃ oil 636 CH CF₃ 0 O CON(CH₂CH₃)CH2CH₂CH₃ oil 637 CH CF₃ 0 O CON(CH₂CH₃)CH₂OCH₃ oil 638 CH CF₃ 0 O CONHCH₂CH₂SCH₂CH₃ oil 639 CH CF₃ 0 O CONHCH(CH₃)CH₂COOCH₂CH₃ oil 640 CH CF₃ 0 O CONH-4-COOCH₃—C₆H₄ 189-191 641 CH CF₃ 0 O CONH-4-CONH₂—C₆H₄ 265-267 642 CH CF₃ 0 O CONHCH₂CH₂Br oil 643 CH CF₃ 0 O CONHCH₂CH═CHCH₂Cl oil 644 CH CF₃ 0 O CONH-4-CONHCH₃—C₆H₄ 219-221 645 CH CF₃ 0 O CONHCH₂CH₂CH₂Br oil 646 CH CF₃ 0 O CONHCH₂CH₂CH₂OCH₃ oil 647 CH CF₃ 0 O CONH-4-CH₂CH₃—C₆H₄ 97-99 648 CH CF₃ 0 O CONHCH₂CH₂OCH(CH₃)₂ oil 649 CH CF₃ 0 O CONHCH₂CH₂CH₂OCH₂CH₃ oil 650 CH CF₃ 0 O

oil 651 CH CF₃ 0 O

64-66 652 CH CF₃ 0 O

oil 653 CH CF₃ 0 O

oil 654 CH CF₃ 0 O CH₂CON(CH₃)CH₂CH₃ oil 655 CH CF₃ 0 O CH₂CON(CH₃)₂ 58-60 656 CH CF₃ 0 O CH₂CON(CH₂)₄ 101-103 657 CH CF₃ 0 O

oil 658 CH CF₃ 0 O

90-92 659 CH CF₃ 0 O CH₂CONHCH₂CH₃ 104-106 660 CH CF₃ 0 O CH₂CON(CH₃)CH₂CH₂OH oil 661 CH CF₃ 0 O CH₂CON(CH₃)CH₂CH₂CH₃ oil 662 CH CF₃ 0 O CH₂CON(CH₃)CH₂CH(—OCH₂CH₂O—) oil 663 CH CF₃ 0 O CH₂CONHCH₂CH₃ 104-106 664 CH CF₃ 0 O CH₂CON(CH₃)CH₂CH₂OH oil 665 CH CF₃ 0 O CH₂CON(CH₃)CH₂CH₂CH₃ oil 667 CH CF₃ 0 O CH₂CON(CH₃)CH₂CH(—OCH₂CH₂O—) oil 668 CH CF₃ 0 O

79-81 669 CH CF₃ 0 O CH₂CONHCH₂CH₂SCH₃ 65-67 670 CH CF₃ 0 O CH₂CONHCH(CH₃)CH₂OCH₃ 86-88 671 CH CF₃ 0 O CON(CH₃)CH₂CH2OCO-c-C₄H₇ oil 672 CH CF₃ 0 O CH₂CONHCH₂CH₂Br 87-89 673 CH CF₃ 0 O CON(CH₃)CH₂CH₂OCOC₆H₅ oil 674 CH CF₃ 0 O CON(CH₃)CH₂CH₂OCO-c-C₃H₅ oil 675 CH CF₃ 0 O CONH-2-CH₃—C₆H₄ 104-106 676 CH CF₃ 0 O CH₂CON(i-C₃H₇)-4-F—C₆H₄ 102-104 677 CH CF₃ 0 O

oil 678 CH CF₃ 0 O

oil 679 CH CF₃ 0 O CON(CH₃)CH₂CH₂OCONHC₆H₅ 100-102 680 CH CF₃ 0 O CON(CH₃)CH₂CH₂OCONHCH₂CH₃ oil 681 CH CF₃ 0 O CON(CH₃)CH₂CH₂OSO₂CH₃ oil 682 CH CF₃ 0 O CH₂CONH-c-C₄H₇ 133-135 683 CH CF₃ 0 O CH₂CONHCH₂CN 158-160

TABLE 2

m.p. No. X Y W R¹ [° C.] 684 N (CF₂)₃CHF₂ O CH₃ 685 N (CF₂)₂CF₃ O CH₂CH₃ 686 N (CF₂)₂CF₃ O COOCH₂CH₃ 687 N (CF₂)₂CF₃ O OH 688 N (CF₂)₂CF₃ O OCH₃ 689 N CF₂CF₃ O CH₃ 690 N CF₂CF₃ O CH₂CH₃ 691 N CF₂CF₃ S CH₃ 692 N CF₂CF₃ S CH₂CH₃ 693 N CF₂CF₃ S (CH₂)₂CH₃ 694 CH CF₃ O CH₃ oil 695 CH CF₃ O CH₂CH₃ 696 CH CF₃ O (CH₂)₂CH₃ 697 CH CF₃ O CH(CH₃)₂ 698 CH CF₃ O (CH₂)₃CH₃ 699 CH CF₃ O CH(CH₃)CH₂CH₃ 700 CH CF₃ O CH₂CH(CH₃)₂ 701 CH CF₃ O C(CH₃)₃ oil 702 CH CF₃ O (CH₂)₄CH₃ 703 CH CF₃ O CH(CH₃)(CH₂)₂CH₃ 704 CH CF₃ O (CH₂)₂CH(CH₃)₂ 705 CH CF₃ O CH₂C(CH₃)₃ 706 CH CF₃ O Cyclo-C₅H₉ 707 CH CF₃ O Cyclo-C₆H₁₁ 708 CH CF₃ O CHO 709 CH CF₃ O CH═CH₂ 710 CH CF₃ O CH₂CH═C(CH₃)₂ 711 CH CF₃ O CH₂CH═CH₂ 712 CH CF₃ O C(CH₃)═CH₂ 713 CH CF₃ O (CH₂)₅C═CH₂ 714 CH CF₃ O C(═CHCH₃)CH₃ 715 CH CF₃ O CH₂C≡CH 716 CH CF₃ O CH₂CH₂C≡CH 717 CH CF₃ O CH₂C≡CCH₂CH₃ 718 CH CF₃ O (CH₂)₄C≡CH 719 CH CF₃ O CHFCF₃ 720 CH CF₃ O COOCH₂CH₃ 721 CH CF₃ O CH₂CH₂OH 722 CH CF₃ O CH₂CH₂OCH₃ 723 CH CF₃ O CH₂COOC(CH₃)₃ 724 CH CF₃ O CH₂SC₆H₅ 725 CH CF₃ O CH₂CONHCH₃ 726 CH CF₃ O CH₂CH(OH)CH₂OH 727 CH CF₃ O CH₂COCH₃ 728 CH CF₃ O COCH3 729 CH CF₃ O CH₂OC₆H₅ 730 CH CF₃ O COC₆H₅ 731 CH CF₃ O CF₂CH₃ 732 CH CF₃ O CH₂CN 733 CH CF₃ O CH₂CH(—O—)CH₂ 734 CH CF₃ O CH₂(4-OCH₃)C₆H₅ 735 CH CF₃ O CH₂CH(OH)CH₂SC₆H₅ 736 CH CF₃ O CH═CF₂ 737 CH CF₃ O CCl═CHCl 738 CH CF₃ O 2-Pyridyl 739 CH CF₃ O OC₆H₅ 740 CH CF₃ O OH 741 CH CF₃ O OCH₃ 742 CH CF₃ O OCH₂CH₃ 743 CH CF₃ O OCHF₂ 744 CH CF₃ O OCH₂C₆H₅ 745 CH CF₃ O SCH₃ 746 CH CF₃ O SC₆H₅ 747 CH CF₃ O NH₂ 748 CH CF₃ O NHCH₃ 749 CH CF₃ O NHCH₂CH₃ 750 CH CF₃ O N(CH₂CH₃)₂ 751 CH CF₃ O N(CH₂CN)₂ 752 CH CF₃ O N(CH₃)₂ 753 CH CF₃ O NHCOCH₃ 754 CH CF₃ O NHCOCH₂CH₃ 755 CH CF₃ O OSO₂CH₃ 756 CH CF₃ O SOCH₂(4-Br)—C₆H₄ 757 CH CF₃ O N(CH₃)COOCH₂C₆H₅ 758 N CF₃ O CH₃ 759 N CF₃ O CH₂CH₃ 760 N CF₃ O (CH₂)₂CH₃ 761 N CF₃ O CH(CH₃)₂ 762 N CF₃ O (CH₂)₃CH₃ 763 N CF₃ O CH₂CH(CH₃)₂ 764 N CF₃ O C(CH₃)₃ 765 N CF₃ O CH₂C(CH₃)₃ 766 N CF₃ O Cyclo-C₅H₉ 767 N CF₃ O Cyclo-C₆H₁₁ 768 N CF₃ O CH₂C═C(CH₃)₂ 769 N CF₃ O CH₂CH₂C═CH₂ 770 N CF₃ O CH₂CH═CH₂ 771 N CF₃ O (CH₂)₅CH═CH₂ 772 N CF₃ O CH₂C≡CH 773 N CF₃ O CH₂C≡CCH₂CH₃ 774 N CF₃ O CHFCF₃ 775 N CF₃ O COOCH₂CH₃ 776 N CF₃ O CH₂CH₂OH 777 N CF₃ O CH₂CH₂OCH₃ 778 N CF₃ O CH₂COOC(CH₃)₃ 779 N CF₃ O CH₂SC₆H₅ 780 N CF₃ O CH₂CONHCH₃ 781 N CF₃ O CH₂CH(OH)CH₂OH 782 N CF₃ O CHO 783 N CF₃ O COCH₃ 784 N CF₃ O CH₂OC₆H₅ 785 N CF₃ O COC₆H₅ 786 N CF₃ O CF₂CH₃ 787 N CF₃ O CH₂CN 788 N CF₃ O CH₂CH₂CN 789 N CF₃ O CH═CF₂ 790 N CF₃ O 2-Furyl 791 N CF₃ O OH 792 N CF₃ O OCH₃ 793 N CF₃ O OCH₂CH₃ 794 N CF₃ O OCHF₂ 795 N CF₃ O OCH₂C₆H₅ 796 N CF₃ O NH₂ 797 N CF₃ O NHCH₃ 798 N CF₃ O NHCH₂CH₃ 799 N CF₃ O N(CH₂CH₃)₂ 800 N CF₃ O N(CH₂CN)₂ 801 N CF₃ O N(CH₃)₂ 802 N CF₃ O NHCOCH₃ 803 N CF₃ O NHCOCH₂CH₃ 804 N CF₃ O OSO₂CH₃ 805 CH CF₃ S CH₃ 806 CH CF₃ S CH₂CH₃ 807 CH CF₃ S (CH₂)₂CH₃ 808 CH CF₃ S CHO 809 CH CF₃ S CHFCF₃ 810 CH CF₃ S CH₂C≡CH 811 CH CF₃ S COOCH₂CH₃ 812 CH CF₃ S CH₂COOC(CH₃)₃ 813 CH CF₃ S CH₂CN 814 N CF₃ S CH₃ 815 N CF₃ S CH₂CH₃ 816 N CF₃ S (CH₂)₂CH₃ 817 N CF₃ S CHFCF₃ 818 N CF₃ S CH₂CH₂OH 819 N CF₃ S CH₂COOC(CH₃)₃ 820 N CH₂CH₂Cl O CH₂CH₃ 821 N CH₂CH₂Cl O NH₂ 822 N CH₂Cl O CH₃ 823 CH CHF₂ O CH₃ 824 CH CHF₂ O CH₂CH₃ 825 CH CHF₂ O (CH₂)₂CH₃ 826 CH CHF₂ O CH₂C═CH₂ 827 CH CHF₂ O C(CH₃)═CH₂ 828 CH CHF₂ O COOCH₂CH₃ 829 CH CHF₂ O CH₂CONHCH₃ 830 CH CHF₂ O CF₂CH₃ 831 CH CHF₂ O CHO 832 CH CHF₂ O NH₂ 833 CH CHF₂ O NHCOCH₃ 834 N CHF₂ O CH₃ 835 N CHF₂ O CH₂CH₃ 836 N CHF₂ O CH(CH₃)(CH₂)₄CH₃ 837 N CHF₂ O CH₂CH═CH₂ 838 N CHF₂ O COOCH₂CH₃ 839 N CHF₂ O NH₂

TABLE 3

m.p. No. X Y m V R¹ [° C.]  840 N (CF₂)₃CHF₂ 0 O CH₃  841 N (CF₂)₂CF₃ 0 O CH₂CH₃  842 N (CF₂)₂CF₃ 0 O COOCH₂CH₃  843 N (CF₂)₂CF₃ 0 O SH  844 N (CF₂)₂CF₃ 0 O SCH₃  845 N (CF₂)₂CF₃ 0 O SCH₂C≡CH  846 N CF₂CF₃ 0 O CH₃  847 N CF₂CF₃ 0 O CH₂CH₃  848 N CF₃ 0 O CH₃  849 N CF₃ 0 O CH₂CH₃  850 N CF₃ 0 O (CH₂)₂CH₃  851 N CF₃ 0 O CH(CH₃)₂  852 N CF₃ 0 O (CH₂)₃CH₃  853 N CF₃ 0 O CH₂CH(CH₃)₂  854 N CF₃ 0 O C(CH₃)₃  855 N CF₃ 0 O CH₂C(CH₃)₃  856 N CF₃ 0 O Cyclo-C₅H₉  857 N CF₃ 0 O Cyclo-C₆H₁₁  858 N CF₃ 0 O CH₂CH═C(CH₃)₂  859 N CF₃ 0 O CH₂CH₂CH═CH₂  860 N CF₃ 0 O CH₂CH═CH₂  861 N CF₃ 0 O (CH₂)₅CH═CH₂  862 N CF₃ 0 O CH₂C≡CH  863 N CF₃ 0 O CH₂C≡CCH₂CH₃  864 N CF₃ 0 O CHFCF₃  865 N CF₃ 0 O COOCH₂CH₃  866 N CF₃ 0 O CH₂CH₂OH  867 N CF₃ 0 O CH₂CH₂OCH₃  868 N CF₃ 0 O CH₂COOC(CH₃)₃  869 N CF₃ 0 O CH₂SPh  870 N CF₃ 0 O CH₂CONHCH₃  871 N CF₃ 0 O CH₂CH(OH)CH₂OH  872 N CF₃ 0 O CHO  873 N CF₃ 0 O COCH₃  874 N CF₃ 0 O CH₂OC₆H₅  875 N CF₃ 0 O COPh  876 N CF₃ 0 O CF₂CH₃  877 N CF₃ 0 O CH₂CN  878 N CF₃ 0 O CH₂CH₂CN  879 N CF₃ 0 O CH═CF₂  880 N CF₃ 0 O 2-Furyl  881 N CF₃ 0 O OH  882 N CF₃ 0 O OCH₃  883 N CF₃ 0 O OCH₂CH₃  884 N CF₃ 0 O OCHF₂  885 N CF₃ 0 O OCH₂Ph  886 N CF₃ 0 O NH₂  887 N CF₃ 0 O NHCH₃  888 N CF₃ 0 O NHCH₂CH₃  889 N CF₃ 0 O N(CH₂CH₃)₂  890 N CF₃ 0 O N(CH₂CN)₂  891 N CF₃ 0 O N(CH₃)₂  892 N CF₃ 0 O NHCOCH₃  893 N CF₃ 0 O NHCOCH₂CH₃  894 N CF₃ 0 O OSO₂CH₃  895 N CH₂CH₂Cl 0 O CH₂CH₃  896 N CH₂CH₂Cl 0 O NH₂  897 N CH₂Cl 0 O CH₃  898 N CHF₂ 0 O CH₃  899 N CHF₂ 0 O CH₂CH₃  900 N CHF₂ 0 O CH(CH₃)(CH₂)₄CH₃  901 N CHF₂ 0 O CH₂CH═CH₂  902 N CHF₂ 0 O COOCH₂CH₃  903 N CHF₂ 0 O NH₂  904 CH CF₃ 0 O CH₃ 60-61  905 CH CF₃ 1 O CH₃  906 CH CF₃ 0 O CH₂CH₃ oil  907 CH CF₃ 1 O CH₂CH₃ oil  908 CH CF₃ 0 O (CH₂)₂CH₃ oil  909 CH CF₃ 1 O (CH₂)₂CH₃ oil  910 CH CF₃ 0 O CH(CH₃)₂  911 CH CF₃ 1 O CH(CH₃)₂  912 CH CF₃ 0 O (CH₂)₃CH₃  913 CH CF₃ 1 O (CH₂)₃CH₃  914 CH CF₃ 0 O CH(CH₃)CH₂CH₃  915 CH CF₃ 1 O CH(CH₃)CH₂CH₃  916 CH CF₃ 0 O CH₂CH(CH₃)₂  917 CH CF₃ 1 O CH₂CH(CH₃)₂  918 CH CF₃ 0 O C(CH₃)₃  919 CH CF₃ 1 O C(CH₃)₃  920 CH CF₃ 0 O (CH₂)₄CH₃  921 CH CF₃ 1 O (CH₂)₄CH₃  922 CH CF₃ 0 O CH(CH₃)(CH₂)₂CH₃  923 CH CF₃ 0 O (CH₂)₂CH(CH₃)₂  924 CH CF₃ 0 O CH₂C(CH₃)₃  925 CH CF₃ 0 O cyclo-C₅H₉  926 CH CF₃ 0 O cyclo-C₆H₁₁  927 CH CF₃ 0 O CH₂(3-Thienyl) oil  928 CH CF₃ 0 O CHO  929 CH CF₃ 0 O CH═CH₂  930 CH CF₃ 0 O CH₂Ph 61-63  931 CH CF₃ 0 O CH₂CH═C(CH₃)₂  932 CH CF₃ 0 O CH₂CH═CH₂  933 CH CF₃ 0 O C(CH₃)═CH₂  934 CH CF₃ 0 O (CH₂)₅C═CH₂  935 CH CF₃ 0 O C(═CHCH₃)CH₃  936 CH CF₃ 0 O CH₂C≡CH  937 CH CF₃ 0 O CH₂CH₂C≡CH₂  938 CH CF₃ 0 O CH₂C≡CCH₂CH₃  939 CH CF₃ 0 O (CH₂)₄C≡CH  940 CH CF₃ 0 O CHFCF₃  941 CH CF₃ 0 O COOCH₂CH₃  942 CH CF₃ 0 O CH₂CH₂OH  943 CH CF₃ 0 O CH₂CH₂OCH₃  944 CH CF₃ 0 O CH₂COOC(CH₃)₃  945 CH CF₃ 0 O CH₂SPh  946 CH CF₃ 0 O CH₂CONHCH₃  947 CH CF₃ 0 O CH₂CH(OH)CH₂OH  948 CH CF₃ 0 O CH₂COCH₃  949 CH CF₃ 0 O COCH3  950 CH CF₃ 0 O CH₂Oph  951 CH CF₃ 0 O COPh  952 CH CF₃ 0 O CF₂CH₃  953 CH CF₃ 0 O CH₂CN oil  954 CH CF₃ 0 O CH₂CH(—O—)CH₂  955 CH CF₃ 0 O CH₂(4-OCH₃)Ph  956 CH CF₃ 0 O CH₂CH(OH)CH₂SPh  957 CH CF₃ 0 O CH═CF₂  958 CH CF₃ 0 O CCl═CHCl  959 CH CF₃ 0 O Ph 120-121  960 CH CF₃ 0 O 2-Thienyl 87-89  961 CH CF₃ 0 O OPh  962 CH CF₃ 0 O OH  963 CH CF₃ 0 O OCH₃  964 CH CF₃ 0 O OCH₂CH₃  965 CH CF₃ 0 O OCHF₂  966 CH CF₃ 0 O OCH₂Ph  967 CH CF₃ 0 O SCH₃  968 CH CF₃ 0 O SPh  969 CH CF₃ 0 O NH₂ 190-191  970 CH CF₃ 0 O NHCH₃  971 CH CF₃ 0 O NHCH₂CH₃  972 CH CF₃ 0 O N(CH₂CH₃)₂  973 CH CF₃ 0 O N(CH₂CN)₂  974 CH CF₃ 0 O N(CH₃)₂  975 CH CF₃ 0 O NHCOCH₃  976 CH CF₃ 0 O NHCOCH₂CH₃  977 CH CF₃ 0 O OSO₂CH₃  978 CH CF₃ 0 O SOCH₂(4-Br)—C₆H₄  979 CH CF₃ 0 O N(CH₃)COOCH₂Ph  980 CH CF₃ 0 NCH₃ CH₃  981 CH CF₃ 0 NCH₂CH₃ CH₃  982 CH CF₃ 0 NCH₂CH₃ CH₂CH₃  983 CH CF₃ 0 NCH₂CN CH₂CH₃  984 CH CF₃ 0 NCH₂OCH₃ NHCH₃  985 CH CF₃ 0 NCH₂OCH₂CH₃ CN  986 CH CF₃ 0 NCH₂CH═CH₂ CH₃  987 CH CF₃ 0 NCH₂CH═CF₂ SCH₃  988 CH CF₃ 0 NCH₂OCH₃ SCH₂CH₃  989 CH CF₃ 0 NCH₂OCH₃ SCH₂Ph  990 CH CHF₂ 0 O CH₃  991 CH CHF₂ 0 O CH₂CH₃  992 CH CHF₂ 0 O (CH₂)₂CH₃  993 CH CHF₂ 0 O CH₂CH═CH₂  994 CH CHF₂ 0 O C(CH₃)═CH₂  995 CH CHF₂ 0 O COOCH₂CH₃  996 CH CHF₂ 0 O CH₂CONHCH₃  997 CH CHF₂ 0 O CF₂CH₃  998 CH CHF₂ 0 O CHO  999 CH CHF₂ 0 O NH₂ 1000 CH CHF₂ 0 O NHCOCH₃ 1001 N CF₂CF₃ 0 S CH₃ 1002 N CF₂CF₃ 0 S CH₂CH₃ 1003 N CF₂CF₃ 0 S (CH₂)₂CH₃ 1004 N CF₃ 0 S CH₃ 1005 N CF₃ 0 S CH₂CH₃ 1006 N CF₃ 0 S (CH₂)₂CH₃ 1007 N CF₃ 0 S CHFCF₃ 1008 N CF₃ 0 S CH₂CH₂OH 1009 N CF₃ 0 S CH₂COOC(CH₃)₃ 1010 CH CF₃ 0 S CH₃ 1011 CH CF₃ 0 S CH₂CH₃ 1012 CH CF₃ 0 S (CH₂)₂CH₃ 1013 CH CF₃ 0 S CHO 1014 CH CF₃ 0 S CHFCF₃ 1015 CH CF₃ 0 S CH₂C≡CH 1016 CH CF₃ 0 S COOCH₂CH₃ 1017 CH CF₃ 0 S CH₂COOC(CH₃)₃ 1018 CH CF₃ 0 S CH₂CN

TABLE 4

m.p. No. X Y m V R² R³ [° C.] 1019 N (CF₂)₃CHF₂ 0 S H CH₂CH₃ 1020 N CF₂CF₂CF₃ 0 S H CH₂CH₃ 1021 N CF₂CF₃ 0 S H CH₂CH₃ 1022 N CH₂CH₂Cl 0 S H CH₂CH₃ 1023 N CH₂Cl 0 S H CH₂CH₃ 1024 N CF₃ 0 S CH₂CH₃ CH₂CH₃ 1025 N CF₃ 0 S (CH₂)₂CH₃ H 1026 N CF₃ 0 S CH(CH₃)₂ H 1027 N CF₃ 0 S CH₂CH(CH₃)₂ H 1028 N CF₃ 0 S C(CH₃)₃ H 1029 CH CF₃ 0 S H CH₃ oil 1030 CH CF₃ 0 S H CH₂CH₃ oil 1031 CH CF₃ 0 S H C(CH₃)₃ oil 1032 CH CF₃ 0 S CH₂CH₃ COOCH₂CH₃ 1033 CH CF₃ 0 S (CH₂)₂CH₃ COOCH₂CH₃ 1034 CH CF₃ 0 S CH(CH₃)₂ COOCH₂CH₃ 1035 CH CF₃ 0 S CH(CH₃)₂ CONHCH₂CH₃ 1036 CH CF₃ 0 S CH(CH₃)₂ CONHCH₂CH₃ 1037 CH CF₃ 0 S CH(CH₃)₂ CON(CH₂CH₃)₂ 1038 CH CF₃ 0 S CH(CH₃)₂ CONH-cyclo-C₃H₇ 1039 CH CF₃ 0 S C(CH₃)₃ COOCH₂CH₃ 1040 CH CF₃ 0 S H CONHCH₂CH₃ 1041 CH CF₃ 0 S H CON(CH₂CH₃)₂ 1042 CH CF₃ 0 S H COOCH₂CH₃ oil 1043 CH CF₃ 0 S H CH₂COOCH₂CH₃ oil 1044 CH CF₃ 0 S H CH₂CHO 1045 CH CF₃ 0 S H CH₂OCH₃ 1046 CH CF₃ 0 S H CH₂OCH₂Ph 1047 CH CF₃ 0 S H H 1048 CH CF₃ 0 S Cyclo-C₅H₉ H 1049 CH CF₃ 0 S CON(CH₃)₂ CH₃ oil 1050 CH CF₃ 0 S CH₃ CH₂CH₂OH 1051 CH CF₃ 0 S CH₃ CH₂CH₂OCH₃ 1052 CH CF₃ 0 S CH₃ CH₂CH₂OCH₂Ph 1053 CH CF₃ 0 S CH₃ CH₂CH₂SPh 1054 CH CF₃ 0 S CH₃ CH₃ oil 1055 CH CF₃ 0 S CH₃ CH₂CH₂CHO 1055 CH CF₃ 0 S CH₃ CH₂CH₂CHNPh 1057 CH CF₃ 0 S CH₃ CH₂CH₂CONH₂ 1058 CH CF₃ 0 S H (4-CF₃O)C₆H₄ 120-121 1059 CH CF₃ 0 S CH₂C≡CH H 1060 CH CF₃ 0 S CH₂CH₂C≡CH H 1061 CH CF₃ 0 S CH₂C≡CCH₂CH₃ H 1062 CH CF₃ 0 S CH₂CH═C(CH₃)₂ H 1063 CH CF₃ 0 S CH₂CH₂CH═CH₂ H 1064 CH CF₃ 0 S CH₂CH═CH₂ H 1065 CH CF₃ 0 S C(CH₃)═CH₂ H 1066 CH CF₃ 0 S CHFCF₃ H 1067 CH CF₃ 0 S COOCH₂CH₃ H 1068 CH CF₃ 0 S CH₂CH₂OH H 1069 CH CF₃ 0 S CH₂CH₂OCH₃ H 1070 CH CF₃ 0 S CH₂COOC(CH₃)₃ H 1071 CH CF₃ 0 S CH₂COCH₃ H 1072 CH CF₃ 0 S COCH3 H 1073 CH CF₃ 0 S CH₂Oph H 1074 CH CF₃ 0 S COPh H 1075 CH CF₃ 0 S CO(4-Cl)—C₆H₄ H 1076 CH CF₃ 0 S CF₂CH₃ H 1077 CH CF₃ 0 S CH₂CN H 1078 CH CF₃ 0 S CH₂CH₂CN H 1079 N CF₃ 0 S H H 1080 N CF₃ 0 S H CH₂CH₂CN 1081 N CF₃ 0 S H CH₂CO₂C(CH₃)₃ 1082 N CF₃ 0 S H CH₂CHO 1083 N CF₃ 0 S H CH₂CH₂OH 1084 N CF₃ 0 S H CH₂CH₂OCH₃ 1085 N CF₃ 0 S Cyclo-C₅H₉ H 1086 N CF₃ 0 S CH₃ COOCH₂CH₃ 1087 N CF₃ 0 S CH₃ COOH 1088 N CF₃ 0 S CH₃ CONH₂ 1089 N CF₃ 0 S CH₃ CONHCH₂CH₃ 1090 N CF₃ 0 S CH₃ CON(CH₂CH₃)₂ 1091 N CF₃ 0 S CH₃ CONHCH₃ 1092 N CF₃ 0 S CH₃ CONHCH₂CN 1093 N CF₃ 0 S CH₃ CON(CH₂CN)₂ 1094 N CF₃ 0 S CH₃ CON(CH₃)₂ 1095 N CF₃ 0 S CH₂C≡CH OCH₂CH₃ 1096 N CF₃ 0 S CH₂CH₂C≡CH OCH₂CH₃ 1097 N CF₃ 0 S CH₂C≡CCH₂CH₃ OCH₂CH₃ 1098 N CF₃ 0 S CH₂CH═C(CH₃)₂ OCH₂CH₃ 1099 N CF₃ 0 S CH₂CH₂CH═CH₂ OCH₂CH₃ 1100 N CF₃ 0 S CH₂CH═CH₂ OCH₂CH₃ 1101 N CF₃ 0 S C(CH₃)═CH₂ OCH₂CH₃ 1102 N CF₃ 0 S CHFCF₃ OCH₂CH₃ 1103 N CF₃ 0 S COOCH₂CH₃ OCH₂CH₃ 1104 N CF₃ 0 S CH₂CH₂OH OCH₂CH₃ 1105 N CF₃ 0 S CH₂CH₂OCH₃ OCH₂CH₃ 1106 N CF₃ 0 S CH₂COOC(CH₃)₃ OCH₂CH₃ 1107 N CF₃ 0 S CH₂COCH₃ H 1108 N CF₃ 0 S COCH3 H 1109 N CF₃ 0 S CH₂Oph H 1110 N CF₃ 0 S COPh H 1111 N CF₃ 0 S CO(4-Cl)—C₆H₄ H 1112 N CF₃ 0 S CF₂CH₃ H 1113 N CF₃ 0 S CH₂CN H 1114 N CF₃ 0 S CH₂CH₂CN H 1115 CH CF₃ 0 O CH₂CH₃ CH₂CH₃ 1116 CH CF₃ 0 O (CH₂)₂CH₃ H 1117 CH CF₃ 0 O H CH₂CH₃ oil 1118 CH CF₃ 0 O CH(CH₃)₂ COOCH₂CH₃ 1119 CH CF₃ 0 O CH(CH₃)₂ COOH 1120 CH CF₃ 0 O CH(CH₃)₂ CONH₂ 1121 CH CF₃ 0 O CH(CH₃)₂ CH₃ 1122 CH CF₃ 0 O C(CH₃)₃ H 1123 CH CF₃ 0 O H CH₃ 1124 CH CF₃ 0 O H cyclo-C₅H₉ 1125 CH CF₃ 0 O H CH₂CH₂CH₃ 1126 CH CF₃ 0 O H Ph  103-1041 1127 CH CF₃ 0 O H 2-Pyridyl 1128 CH CF₃ 0 O H 2-Furyl 1129 CH CF₃ 0 O Cyclo-C₅H₉ H 1130 CH CF₃ 0 O CH₃ COOCH₂CH₃ 1131 CH CF₃ 0 O CH₃ COOH 1132 CH CF₃ 0 O CH₃ CONH₂ 1133 CH CF₃ 0 O CH₃ CONHCH₂CH₃ 1134 CH CF₃ 0 O CH₃ CON(CH₂CH₃)₂ 1135 CH CF₃ 0 O CH₃ CONHCH₃ 1136 CH CF₃ 0 O CH₃ CONHCH₂CN 1137 CH CF₃ 0 O CH₃ CON(CH₂CN)₂ 1138 CH CF₃ 0 O CH₃ CON(CH₃)₂ 1139 CH CF₃ 0 O CH₂C≡CH H 1140 CH CF₃ 0 O CH₂CH₂C≡CH H 1141 CH CF₃ 0 O CH₂C≡CCH₂CH₃ H 1142 CH CF₃ 0 O CH₂CH═C(CH₃)₂ H 1143 CH CF₃ 0 O CH₂CH₂C═CH H 1144 CH CF₃ 0 O CH₂CH═CH₂ H 1145 CH CF₃ 0 O C(CH₃)═CH₂ H 1146 CH CF₃ 0 O CHFCF₃ H 1147 CH CF₃ 0 O COOCH₂CH₃ H 1148 CH CF₃ 0 O CH₂CH₂OH H 1149 CH CF₃ 0 O CH₂CH₂OCH₃ H 1150 CH CF₃ 0 O CH₂COOC(CH₃)₃ H 1151 CH CF₃ 0 O CH₂COCH₃ H 1152 CH CF₃ 0 O COCH3 H 1153 CH CF₃ 0 O CH₂Oph H 1154 CH CF₃ 0 O COPh H 1155 CH CF₃ 0 O CO(4-Cl)—C₆H₄ H 1156 CH CF₃ 0 O CF₂CH₃ H 1157 CH CF₃ 0 O CH₂CN H 1158 CH CF₃ 0 O CH₂CH₂CN H 1159 N CF₃ 0 O CH₂CH₃ CH₂CH₃ 1160 N CF₃ 0 O (CH₂)₂CH₃ H 1161 N CF₃ 0 O CH(CH₃)₂ CONH₂ 1162 N CF₃ 0 O CH(CH₃)₂ CH₃ 1163 N CF₃ 0 O C(CH₃)₃ H 1164 N CF₃ 0 O H CH₃ 1165 N CF₃ 0 O H CH₂CH₃ 1166 N CF₃ 0 O H CH₂CH₂CH₃ 1167 N CF₃ 0 O H Ph 1168 N CF₃ 0 O H 2-Pyridyl 1169 N CF₃ 0 O H 2-Furyl 1170 N CF₃ 0 O Cyclo-C₅H₉ H 1171 N CF₃ 0 O CH₃ COOCH₂CH₃ 1172 N CF₃ 0 O CH₃ COOH 1173 N CF₃ 0 O CH₃ CONH₂ 1174 N CF₃ 0 O CH₃ CONHCH₂CH₃ 1175 N CF₃ 0 O CH₃ CON(CH₂CH₃)₂ 1176 N CF₃ 0 O CH₃ CONHCH₃ 1177 N CF₃ 0 O CH₃ CONHCH₂CN 1178 N CF₃ 0 O CH₃ CON(CH₂CN)₂ 1179 N CF₃ 0 O CH₃ CON(CH₃)₂ 1180 N CF₃ 0 O CH₂C≡CH H 1181 N CF₃ 0 O CH₂CH₂C≡CH H 1182 N CF₃ 0 O CH₂C≡CCH₂CH₃ H 1183 N CF₃ 0 O CH₂CH═C(CH₃)₂ H 1184 N CF₃ 0 O CH₂CH₂CH═CH₂ H 1185 N CF₃ 0 O CH₂CH═CH₂ H 1186 N CF₃ 0 O C(CH₃)═CH₂ H 1187 N CF₃ 0 O CHFCF₃ H 1188 N CF₃ 0 O COOCH₂CH₃ H 1189 N CF₃ 0 O CH₂CH₂OH H 1190 N CF₃ 0 O CH₂CH₂OCH₃ H 1191 N CF₃ 0 O CH₂COOC(CH₃)₃ H 1192 N CF₃ 0 O CH₂COCH₃ H 1193 N CF₃ 0 O COCH3 H 1194 N CF₃ 0 O OCH₂Oph H 1195 N CF₃ 0 O COPh H 1196 N CF₃ 0 O CO(4-Cl)—C₆H₄ H 1197 N CF₃ 0 O CF₂CH₃ H 1198 N CF₃ 0 O CH₂CN H 1199 N CF₃ 0 O CH₂CH₂CN H 1200 N CF₃ 0 O CH₂NHSO₂CH₃ CH₃ 1201 N CF₃ 0 O (CH₂)₂NHSO₂CH₃ CH₃ 1202 N CF₃ 0 O CH₂NHSO₂CH₂CH₃ CH₃ 1203 N CF₃ 0 O H CH₂NHSO₂CH₂Ph 1204 CH CF₃ 0 O (CH₂)₄NHSO₂CF₃ CH₃ 1205 CH CF₃ 0 O (CH₂)₂S(CH₂)₂CH₃ CH₂CH₂CH₃ 1206 CH CF₃ 0 O (CH₂)₄S(CH₂)₄0CH₃ CH₃ 1207 CH CF₃ 0 S CH₃ (CH₂)₂S(CH₂)₂CN 1208 CH CF₃ 0 S CH₂NHSO₂CH₂CH₃ CH₃ 1209 CH CF₃ 0 S CH₂NHSO₂CH₂Ph CH₂CH₂CH₃ 1210 CH CF₃ 0 S (CH₂)₂NHSO₂CH₃ CF₃ 1211 CH CF₃ 0 S H CH₂NHSO₂CH₃ 1212 CH CF₃ 0 S CH(CH₃)CH₂NHPh CF₃ 1213 CH CF₃ 0 S (CH₂)₂S(2-F)—C₆H₄ CH₂CH₂CH₃ 1214 CH CF₃ 0 S (CH₂)₆NHCH₂)₆OCH₃ CF₃ 1215 CH CF₃ 0 S H (CH₂)₂NH—(2-F)—C₆H₄ 1216 CH CF₃ 0 S (CH₂)₃NHCH₂CN H 1217 CH CF₃ 0 S (CH₂)₂O(3-Cl)—C₆H₄ CH₃ 1218 CH CF₃ 0 S CF₃ (CH₂)₆NHCH₂CF₃ 1219 CH CF₃ 0 S CH₃ (CH₂)₂O(3-CH₃)—C₆H₄ 1220 CH CF₃ 0 O H CH₂NHPh 1221 CH CF₃ 0 O CH₃ (CH₂)₄S(2-Br)—C₆H₄ 1222 CH CF₃ 0 O (CH₂)₆NH(CH₂)₂OCH₃ CH₃ 1223 CH CF₃ 0 O (CH₂)₂NH(CH₂)₄OCH₃ H 1224 CH CF₃ 0 O CF₃ (CH₂)₃NH—(4-CN)—C₆H₄ 1225 CH CF₃ 0 O (CH₂)₄NHCH₂CF₃ CH₃ 1226 CH CF₃ 0 O C₂F₅ (CH₂)₂O(3-CH₃)—C₆H₄ 1227 CH CF₃ 0 O (CH₂)₄NHCH₂CN H 1228 CH CF₃ 0 O (CH₂)₃O(4-Cl)—C₆H₄ C₂F₅

TABLE 5

m.p. No. X Y V R⁴ R⁵ R⁶ R⁷ [° C.] 1229 CH CF₃ O H H H H oil 1230 CH CF₃ O H H CH₃ H oil 1231 CH CF₃ O H H CH₂CH₃ H oil 1232 CH CF₃ O H H CH(CH₃)₂ H 1233 CH CF₃ O H H CH₂CH(CH₃)₂ H 1234 CH CF₃ O H H CH(CH₃)CH₂CH₃ H 1235 CH CF₃ O H H CH₂OH H 1236 CH CF₃ O H H CH(OH)CH₃ H 1237 CH CF₃ O H H CH₂SH H 1238 CH CF₃ O H H CH₂CH₂SCH₃ H 1239 CH CF₃ O H H (CH₂)₃NH₂ H 1240 CH CF₃ O H H (CH₂)₄NH₂ H 1241 CH CF₃ O H H CH═CH₂ H 1242 CH CF₃ O H H (CH₂)₂COOCH₃ H 1243 CH CF₃ O H H (CH₂)₂COOH H 1244 CH CF₃ O H H (CH₂)₂CONH₂ H 1245 CH CF₃ S CH₃ CH₃ H H 1246 CH CF₃ O H H CH₃ CH₃ oil 1247 CH CF₃ O H H CH₂COOCH₃ H 1248 CH CF₃ O H H CH₂COOH H 1249 CH CF₃ O H H CH₂CONH₂ H 1250 CH CF₃ O H H CH₂Ph H 1251 CH CF₃ O H H CH₂—(4-OH)—C₆H₄ H 1252 CH CF₃ O H H CH₂—(3-Indolyl) H 1253 CH CF₃ O CH₃ CH₃ H H oil 1254 CH CF₃ O CH₃ H H H oil 1255 CH CF₃ O CH₃ H H Ph 1256 CH CF₃ O H (CH₂)₄ H 1257 CH CF₃ NH H (CH₂)₄ H 1258 CH CF₃ NCH₃ H (CH₂)₄ H 1259 CH CF₃ NCH₂C₆H₄ H (CH₂)₄ H 1260 CH CF₃ NCH(CH₃)₂ H (CH₂)₄ H 1261 CH CF₃ O Ph H Ph H 1262 CH CF₃ NH Ph H Ph H 1263 CH CF₃ NCH₃ Ph H Ph H 1264 CH CF₃ NCH₂C₆H₄ Ph H Ph H 1265 N CF₃ O H H CH₂CH₃ H oil 1266 N CF₃ O H H CH(CH₃)₂ H 1267 N CF₃ O H H CH₂CH(CH₃)₂ H 1268 N CF₃ O H H CH₂COOH H 1269 N CF₃ O H H CH₂COOCH₃ H 1270 N CF₃ O H H CH₂CONH₂ H 1271 N CF₃ O CH₃ CH₃ H H 1272 N CF₃ O H (CH₂ H 1273 N CF₃ O H H CH₂CH₂SCH₃ H 1274 CH CF₃ S H H H H oil

TABLE 6

m.p. No. X Y R⁸ R¹ [° C.] 1275 CH CF₃ CH₃ SH 209-210 1276 CH CF₃ CH₃ SCH₃ 1277 CH CF₃ CH₃ SCH₂CH₃ 1278 CH CF₃ CH₃ S(CH₂)₂CH₃ 1279 CH CF₃ CH₃ SCH(CH₃)₂ 1280 CH CF₃ CH₃ SPh 1281 CH CF₃ CH₃ S(CH₂)₃CH₃ 1282 CH CF₃ CH₃ SCH(CH₃)CH₂CH₃ 1283 CH CF₃ CH₃ SCH₂CH(CH₃)₂ 1284 CH CF₃ CH₃ OH 119-120 1285 CH CF₃ CH₃ OCH₃ 1286 CH CF₃ CH₃ OCH₂CH₃ 1287 CH CF₃ CH₃ OCHF₂ 1288 CH CF₃ CH₃ OCH₂Ph 1289 CH CF₃ CH₃ OCONHPh 1290 CH CF₃ CH₃ OCONH—(4-F)—C₆H₄ 1291 CH CF₃ CH₃ OCONH—(3,5-di-Cl)—C₆H₃ 1292 CH CF₃ CH₂CN OCH₃ 1293 CH CF₃ CH₂CN OCH₂CH₃ 1294 CH CF₃ CH₂CN OCHF₂ 1295 CH CF₃ CH₂CN OCH₂Ph 1296 CH CF₃ CH₂CN OCONHPh 1297 CH CF₃ CH₂CN OCONH—(4-F)—C₆H₄ 1298 CH CF₃ CH₂OCH₂CH₃ OCH₃ 1299 CH CF₃ CH₂OCH₂CH₃ OCH₂CH₃ 1300 CH CF₃ CH₂OCH₂CH₃ OCHF₂ 1301 CH CF₃ CH₂OCH₂CH₃ OCH₂Ph 1302 CH CF₃ CH₂OCH₂CH₃ OCONHPh 1303 CH CF₃ H CH₃ 203-204 1304 CH CF₃ H CH₂CH₃ 134-135 1305 CH CF₃ H (CH₂)₂CH₃ 1306 CH CF₃ H CH(CH₃)₂ 1307 CH CF₃ H Cyclo-C₃H₅ 1308 CH CF₃ H (CH₂)₃CH₃ 1309 CH CF₃ H CH(CH₃)CH₂CH₃ 1310 CH CF₃ H CH₂CH(CH₃)₂ 1311 CH CF₃ H CH═CH₂ 1312 CH CF₃ H CH₂CH═C(CH₃)₂ 1313 CH CF₃ H CH₂CH₂CH═CH₂ 1314 CH CF₃ H CH₂CH═CH₂ 1315 CH CF₃ H C(CH₃)═CH₂ 1316 CH CF₃ H CHFCF₃ 1317 CH CF₃ H COOCH₂CH₃ 1318 CH CF₃ H CH₂CH₂OH 1319 CH CF₃ H CH₂CH₂OCH₃ 1320 CH CF₃ H CH₂COOC(CH₃)₃ 1321 CH CF₃ CH₃ CH₂COOC(CH₃)₃ 1322 CH CF₃ CH₂CN CH₂COOC(CH₃)₃ 1323 CH CF₃ CH₂OCH₂CH₃ CH₂COOC(CH₃)₃ 1324 CH CF₃ H CH₂SPh 1325 CH CF₃ H CH₂CONHCH₃ 1326 CH CF₃ H CH₂COCH₃ 1327 CH CF₃ H COCH3 1328 CH CF₃ H CH₂Oph 1329 CH CF₃ H COPh 1330 CH CF₃ H CO(3-Cl)—C₆H₄ 1331 CH CF₃ H CF₂CH₃ 1332 CH CF₃ H CH₂CN 1333 CH CF₃ H CH₂CH₂CN 1334 CH CF₃ H CH₂CH(—O—)CH₂ 1336 CH CF₃ H CH₂(4-OCH₃)Ph 1337 N CF₃ CH₃ SH 1338 N CF₃ CH₃ SCH₃ 1339 N CF₃ CH₃ SCH₂CH₃ 1340 N CF₃ CH₃ SPh 1341 N CF₃ CH₃ SCH₂CH(CH₃)₂ 1342 N CF₃ CH₃ OH 1343 N CF₃ CH₃ OCH₃ 1344 N CF₃ CH₃ OCH₂CH₃ 1345 N CF₃ CH₃ OCH₂Ph 1346 N CF₃ CH₃ OCONHPh 1347 N CF₃ CH₂CN OCH₃ 1348 N CF₃ CH₂CN OCH₂CH₃ 1349 N CF₃ CH₂CN OCH₂Ph 1350 N CF₃ CH₂CN OCONHPh 1351 N CF₃ CH₂OCH₂CH₃ OCH₃ 1352 N CF₃ CH₂OCH₂CH₃ OCH₂Ph 1353 N CF₃ CH₂OCH₂CH₃ OCONHPh 1354 N CF₃ H CH₃ 1355 N CF₃ H CH₂CH₃ 1356 N CF₃ H (CH₂)₂CH₃ 1357 N CF₃ H CH(CH₃)₂ 1358 N CF₃ H (CH₂)₃CH₃ 1359 N CF₃ H CH(CH₃)CH₂CH₃ 1360 N CF₃ H CH₂CH(CH₃)₂ 1361 N CF₃ H CH₂C═C(CH₃)₂ 1362 N CF₃ H CH₂CH═CH₂ 1363 N CF₃ H C(CH₃)H═CH₂ 1364 N CF₃ H COOCH₂CH₃ 1365 N CF₃ H CH₂CH₂OH 1366 N CF₃ H CH₂CH₂OCH₃ 1367 N CF₃ H CH₂COOC(CH₃)₃ 1368 N CF₃ H CH₂SPh 1369 N CF₃ H CH₂CONHCH₃ 1370 N CF₃ H CH₂COCH₃ 1371 N CF₃ H COCH3 1372 N CF₃ H CH₂Oph 1373 N CF₃ H COPh 1374 N CF₃ H CH₂CN 1375 N CF₃ H CH₂CH₂CN 1376 CH CF₃ CH₃ CH₂CH₃ oil

C. Biological Examples

Example 1

A Petri dish whose bottom is covered with filter paper and which contains about 5 ml of culture medium is prepared. Pieces of filter paper with about 30, 24-hour-old eggs of the American tobacco budworm (Heliothis virescens) are dipped into an aqueous solution of the formulated preparation to be examined for 5 seconds and subsequently placed in the Petri dish. A further 200 μl of the aqueous solution are spread over the culture medium. The Petri dish is closed and then kept at about 25° C. in a climatized chamber. After 6 days' storage, the effect of the preparation on the eggs and the larvae which may have hatched from these is determined. At a concentration of 300 ppm (based on the content of active compound), the preparations of Example Nos. 79 and 88 effect a mortality of 90-100%.

Example 2

Germinated broad bean seeds (Vicia faba) with radicles are transferred into brown glass bottles filled with tap water and subsequently populated with approximately 100 black bean aphids (Aphis fabae) belegt. Plants and aphids are then dipped for 5 seconds into an aqueous solution of the formulated preparation to be examined. After the solution has dripped off, plant and animals are kept in a climatized chamber (16 hours of light/day, 25° C., 40-60% relative atmospheric humidity. After 3 and 6 days' storage, the effect of the preparation on the aphids is determined. At a concentration of 300 ppm (based on the content of active compound), the preparations of Example Nos. 79, 78, 80, 81, 83, 84, 88, 133, 135, 136, 137, 138, 139, 1117, 1229, 1230, 1231, 1246 and 1254 effect a mortality of 90-100% among the aphids.

Example 3

The leaves of 12 rice plants having a stem length of 8 cm are dipped for 5 seconds into an aqueous solution of the formulated preparation to be examined. After the solution has dripped off, the rice plants treated in this manner are placed in a Petri dish and populated with approximately 20 larvae (L3 stage) of the rice leaf hopper species Nilaparvata lugens. The Petri dish is closed and stored in a climatized chamber (16 hours of light/day, 25° C., 40-60% relative atmospheric humidity). After 6 days' storage, the mortality among the leaf hopper larvae is determined. At a concentration of 300 ppm (based on the content of active compound), the preparations of Example Nos. 88, 139 and 927 effect a mortality of 90-100%.

Example 4

Germinated broad bean seeds (Vicia faba) with radicles are transferred into brown glass bottles filled with tap water. Four milliliters of an aqueous solution of the formulated preparation to be examined are pipetted into the brown glass bottle. The broad bean is subsequently heavily populated with approximately 100 black bean aphids (Aphis fabae). Plant and animals are then stored in a climatized chamber (16 hours of light/day, 25° C., 40-60% relative atmospheric humidity). After 3 and 6 days' storage, the root-systemic activity of the preparation on the aphids is determined. At a concentration of of 30 ppm (based on the content of active compound), the Preparations of Example Nos. 78, 79, 80, 81, 83, 84, 88, 133, 135, 136, 137, 138, 139, 187, 1117, 1229, 1230, 1231, 1246 and 1254 effect a mortality of 90-100% among the aphids by root-systemic action.

II. COMPOUNDS OF THE FORMULA (I′)

A. Chemical Examples

Example 1

At room temperature, a solution of 4-tridiimidfluoromethylnicotinic acid (2.2 g) in 40 ml of THF was admixed with 1,1-carbonyldiimidazole (1.9 g), and the mixture was heated at 40° C. for 30 min. Furfurylsulfonylacetamidoxime (2.5 g) was then added, and the mixture was stirred at 40° C. for a further 5 h. The reaction mixture was then concentrated under reduced pressure and poured onto ice-water. The resulting precipitate was filtered off with suction and subsequently dried in a drying cabinet. This gave 4-trifluoromethylnicotinic acid furfurylsulfonylacetamidoxime ester in the form of a colorless solid (melting point 171° C.).

¹H-NMR (DMSO-d⁶, 300 MHz): 4.09 (s, 2H), 4.86 (s, 2H), 6.55 (m, 1H), 6.63 (m, 1H), 7.08 (s, 2H), 7.75 (m, 1H), 7.94 (d, J=5 Hz, 1H), 9.07 (d, J=5 Hz, 1H), 9.30 (s, 1H).

Example 2

The amidoxime ester described above (4.0 g) was admixed with 80 ml of toluene and 60 ml of xylene and Amberlyst 15 (1.0 g). The reaction mixture was heated at 125° C. for 6 h. The mixture was subsequently filtered off with suction and the filtrate was concentrated under reduced pressure and purified by chromatography (silica gel, ethyl acetate/petroleum ether, 4:1). Subsequent trituration with n-heptane gave [5-(4′-trifluoromethylpyridin-3′-yl)-[1,2,4]-oxadiazole-3-methyl]furfurylsulfone as a pale yellow solid (melting point 99° C.).

¹H-NMR (CDCl₃, 300 MHz): 4.53 (s, 2H), 4.62 (s, 2H), 6.44 (m, 1H), 6.69 (m, 1H), 7.54 (m, 1H), 7.82 (d, J=5 Hz, 1H), 9.08 (d, J=5 Hz, 1H), 9.40 (s, 1H).

Example 3

A mixture of 3-chloromethyl-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole (1.0 g), sodium sulfite (0.9 g), water (18 ml) and methanol (18 ml) was stirred at 50° C. for 6 hours. The reaction mixture was then concentrated and the residue was taken up in methanol and filtered. The methanol solution was then concentrated and the residue was triturated with diethyl ether. This gave

as a slightly yellowish solid (m.p.=214° C.).

¹H-NMR (DMSO-d⁶, 300 MHz): 4.02 (s, 2H), 8.09 (d, J=5H, 1H), 9.15 (d, J=5 Hz, 1H), 9.33 (s, 1H).

The sodium sulfonate described above (0.95 g) was suspended in phosphorus oxychloride (30 ml), and the mixture was heated at reflux temperature for 5 hours. The excess phosphorus oxychloride was then distilled off and the sulfonyl chloride which remained was taken up in dichloromethane (10 ml). This suspension was admixed with ethylmethylamine (150 ml), and stirring at room temperature was continued for one hour.

The mixture was subsequently washed with water, 5% strength aqueous potassium hydrogen-sulfate solution and saturated sodium bicarbonate solution. The crude product which was obtained after drying (MgSO₄) and concentration of the dichloromethane phase was purified chromatographically. This gave the desired sulfonamide as a colorless oil.

¹H-NMR (CDCl₃, 300 MHz): 1.23 (6, J=7 Hz, 3H), 2.92 (s, 3H), 3.25 (Q, J=7Hz, 2H), 4.54 (s, 2H), 7.90 (d, J=5 Hz, 1H), 9.06 (d, J=5 Hz, 1H), 9.35 (s, 1H).

The sulfonamides listed in Table 1 are prepared in an analogous manner.

Example 4

3-[(2-Hydroxyethyl)thiomethyl]-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

A solution of sodium methoxide (0.31 ml, 30% in methanol) was added to a solution of 3-chloromethyl-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole (0.5 g) and 2-mercaptoethanol (0.13 g) in methanol (5 ml), and the mixture was stirred at room temperature for 5 hours.

Water was then added and the mixture was extracted with ethyl acetate. The organic phase was washed with water, dried (MgSO₄), filtered and concentrated. Chromatographic purification was carried out over silica gel using heptane/ethyl acetate. The crude product gave the desired compound as a slightly brown oil.

¹H-NMR (CDCl₃, 300 MHz): 2.88 (t, J=7 Hz, 2H), 3.04 (b, s, 1H), 3.82 (t, J=7 Hz, 2H), 3.94 (s, 2H), 7.80 (d, J=5 Hz, 1H), 9.04 (d, J=5 Hz, 1H), 9.35 (s, 1H).

Example 5

3-Ethoxymethyl-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

3-Iodomethyl-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole (0.5 g) was dissolved in a freshly prepared solution of sodium ethoxide (30 mg of sodium in 7 ml of ethanol), and the mixture was stirred at room temperature for 6 hours.

The reaction mixture was then concentrated, the residue was taken up in ethyl acetate, washed with water, dried (MgSO₄), filtered and concentrated.

Chromatographic purification of the crude product gave the desired ether as a yellowish oil.

¹H-NMR (CDCl₃, 300 MHz): 1.31 (t, J=7 Hz, 3H), 3.72 (t, J=7 Hz, 2H), 4.76 (s, 2H), 7.70 (d, J=5 Hz, 1H), 9.03 (d, J=5 Hz, 1H), 9.33 (s, 1H).

The ethers listed in Table 1 are prepared in an analogous manner.

Example 6

Ethyl [(4′-(Trifluoromethyl)pyridin-3′-yl)-5-[1,2,4]-oxadiazole-3-methyl]carbonate

3-Hydroxymethyl-5-(4′-(trifluoromethyl)pyridin-3′-yl)-[1,2,4]-oxadiazole (1.0 g) was initially charged in acetonitrile (10 ml), and the mixture was admixed with triethylamine (0.5 g). Ethyl chloroformate (0.5 g) was added, and the mixture was then stirred at room temperature for 6 h. The reaction mixture was then mixed with ethyl acetate (5 ml), washed with 2N sodium carbonate solution and dried over MgSO₄. The crude product which was obtained after the drying agent had been filtered off and the solution had been concentrated under reduced pressure was purified by column chromatography (silica gel, n-heptane/ethyl acetate, 1:1). This gave the target product as an oil.

¹H-NMR (CDCl₃, 300 MHz): 1.38 (t, J=7 Hz, 3H), 4.31 (q, J=7 Hz, 2H), 5.43 (s, 2H), 7.80 (d, J=5 Hz, 1H), 9.04 (d, J=5 Hz, 1H), 9.37 (s, 1H).

TABLE 1

Ex. m.p. No. Y R R′ [° C.]  1 O n-Pr  2 O i-Pr  3 O n-Bu  4 O i-Bu oil  5 O allyl  6 O CH₂C≡CH  7 O CH═CH₂  8 O CH₂CH₂F  9 O CF₃  10 O CH₂CF₃  11 O CH₂CN  12 O cyclopropyl  13 O cyclopropylmethyl  14 O CH₂CO₂Me  15 O CH₂CH₂NMe₂  16 O CH₂-(N-morpholinyl)  17 O 2-chloropyridin-5-yl-methyl  18 O 2-furanyl  19 O 2-pyrimidinyl  20 O 2-oxazolyl  21 O 5-[1,2,4]-oxadiazolyl  22 O tetrazolyl  23 S H  24 S Me  25 S Et  26 S n-Pr  27 S i-Pr  28 S n-Bu  29 S i-Bu  30 S allyl  31 S CH₂C≡CH  32 S CH═CH₂  33 S CH₂CH₂F  34 S CF₃  35 S CH₂CF₃  36 S CH₂CN  37 S cyclopropyl  38 S cyclopropylmethyl  39 S CH₂CO₂Me  40 S CH₂CH₂NMe₂  41 S CH₂-(N-morpholinyl)  42 S 2-chloropyridin-5-yl-methyl  43 S 2-furanyl  44 S 2-pyrimidinyl  45 S 2-oxazolyl  46 S 5-[1,2,4]-oxadiazolyl  47 S tetrazolyl  48 S(O) Me  49 S(O) Et  50 S(O) n-Pr  51 S(O) i-Pr  52 S(O) n-Bu  53 S(O) i-Bu  54 S(O) allyl  55 S(O) CH₂C≡CH  56 S(O) CH═CH₂  57 S(O) CH₂CH₂F  58 S(O) CF₃  59 S(O) CH₂CF₃  60 S(O) CH₂CN  61 S(O) cyclopropyl  62 S(O) cyclopropylmethyl  63 S(O) CH₂CO₂Me  64 S(O) CH₂CH₂NMe₂  65 S(O) CH₂-(N-morpholinyl)  66 S(O) 2-chloropyridin-5-yl-methyl  67 S(O) 2-furanyl  68 S(O) 2-pyrimidinyl  69 S(O) 2-oxazolyl  70 S(O) 5-[1,2,4]-oxadiazolyl  71 S(O) tetrazolyl  72 S(O)₂ Me  73 S(O)₂ Et  74 S(O)₂ n-Pr  75 S(O)₂ i-Pr  76 S(O)₂ n-Bu  77 S(O)₂ i-Bu  78 S(O)₂ allyl  79 S(O)₂ CH₂C≡CH  80 S(O)₂ CH═CH₂  81 S(O)₂ CH₂CH₂F  82 S(O)₂ CF₃  83 S(O)₂ CH₂CF₃  84 S(O)₂ CH₂CN  85 S(O)₂ cyclopropyl  86 S(O)₂ cyclopropylmethyl  87 S(O)₂ CH₂CO₂Me  88 S(O)₂ CH₂CH₂NMe₂  89 S(O)₂ CH₂-(N-morpholinyl)  90 S(O)₂ 2-chloropyridin-5-yl-methyl  91 S(O)₂ 2-furanyl  92 S(O)₂ 2-pyrimidinyl  93 S(O)₂ 2-oxazolyl  94 S(O)₂ 5-[1,2,4]-oxadiazolyl  94a S(O)₂ tetrazolyl  95 OC(O) H  96 OC(O) Me  97 OC(O) Et  98 OC(O) n-Pr  99 OC(O) i-Pr 100 OC(O) n-Bu 101 OC(O) i-Bu 102 OC(O) allyl 103 OC(O) CH₂C≡CH 104 OC(O) CH═CH₂ 105 OC(O) CH₂CH₂F 106 OC(O) CF₃ 107 OC(O) CH₂CF₃ 108 OC(O) CH₂CN 109 OC(O) cyclopropyl 110 OC(O) cyclopropylmethyl 111 OC(O) CH₂CO₂Me 112 OC(O) CH₂CH₂NMe₂ 113 OC(O) CH₂-(N-morpholinyl) 114 OC(O) 2-chloropyridin-5-yl-methyl 115 OC(O) 2-furanyl 116 OC(O) 2-pyrimidinyl 117 OC(O) 2-oxazolyl 118 OC(O) 5-[1,2,4]-oxadiazolyl 119 OC(O) tetrazolyl 120 OC(O)O Me 121 OC(O)O Et 122 OC(O)O n-Pr 123 OC(O)O i-Pr 124 OC(O)O n-Bu 125 OC(O)O i-Bu 126 OC(O)O allyl 127 OC(O)O CH₂C≡CH 128 OC(O)O CH═CH₂ 129 OC(O)O CH₂CH₂F 130 OC(O)O CF₃ 131 OC(O)O CH₂CF₃ 132 OC(O)O CH₂CN 133 OC(O)O cyclopropyl 134 OC(O)O cyclopropylmethyl 135 OC(O)O CH₂CO₂Me 136 OC(O)O CH₂CH₂NMe₂ 137 OC(O)O CH₂-(N-morpholinyl) 138 OC(O)O 2-chloropyridin-5-yl-methyl 139 OC(O)O 2-furanyl 140 OC(O)O 2-pyrimidinyl 141 OC(O)O 2-oxazolyl 142 OC(O)O 5-[1,2,4]-oxadiazolyl 143 OC(O)O tetrazolyl 144 OC(O)O CH₂CH₂OMe 145 OC(O)NR′ H H 146 OC(O)NR′ Me H 147 OC(O)NR′ Et H 148 OC(O)NR′ n-Pr H 149 OC(O)NR′ i-Pr H 150 OC(O)NR′ n-Bu H 151 OC(O)NR′ i-Bu H 152 OC(O)NR′ allyl H 153 OC(O)NR′ CH₂C≡CH H 154 OC(O)NR′ CH═CH₂ H 155 OC(O)NR′ CH₂CH₂F H 156 OC(O)NR′ CF₃ H 157 OC(O)NR″ CH₂CF₃ H 158 OC(O)NR′ CH₂CN H 159 OC(O)NR′ cyclopropyl H 160 OC(O)NR′ cyclopropylmethyl H 161 OC(O)NR′ CH₂CO₂Me H 162 OC(O)NR′ CH₂CH₂NMe₂ H 163 OC(O)NR′ CH₂-(N-morpholinyl) H 164 OC(O)NR′ 2-chloropyridin-5-yl-methyl H 165 OC(O)NR′ 2-furanyl H 166 OC(O)NR′ 2-pyrimidinyl H 167 OC(O)NR′ 2-oxazolyl H 168 OC(O)NR′ 5-[1,2,4]-oxadiazolyl H 169 OC(O)NR′ tetrazolyl H 170 OC(O)NR′ H Me 171 OC(O)NR′ Me Me 172 OC(O)NR′ Et Me 173 OC(O)NR′ n-Pr Me 174 OC(O)NR′ i-Pr Me 175 OC(O)NR′ n-Bu Me 176 OC(O)NR′ i-Bu Me 177 OC(O)NR′ allyl Me 178 OC(O)NR′ CH₂C≡CH Me 179 OC(O)NR′ CH═CH₂ Me 180 OC(O)NR′ CH₂CH₂F Me 181 OC(O)NR′ CF₃ Me 182 OC(O)NR″ CH₂CF₃ Me 183 OC(O)NR′ CH₂CN Me 184 OC(O)NR′ cyclopropyl Me 185 OC(O)NR′ cyclopropylmethyl Me 186 OC(O)NR′ CH₂CO₂Me Me 187 OC(O)NR′ CH₂CH₂NMe₂ Me 188 OC(O)NR′ CH₂-(N-morpholinyl) Me 189 OC(O)NR′ 2-chloropyridin-5-yl-methyl Me 190 OC(O)NR′ 2-furanyl Me 191 OC(O)NR′ 2-pyrimidinyl Me 192 OC(O)NR′ 2-oxazolyl Me 193 OC(O)NR′ 5-[1,2,4]-oxadiazolyl Me 194 OC(O)NR′ tetrazolyl Me 195 OC(O)NR′ H Et 196 OC(O)NR′ Me Et 197 OC(O)NR′ Et Et 198 OC(O)NR′ n-Pr Et 199 OC(O)NR′ i-Pr Et 200 OC(O)NR′ n-Bu Et 201 OC(O)NR′ i-Bu Et 202 OC(O)NR′ allyl Et 203 OC(O)NR′ CH₂C≡CH Et 204 OC(O)NR′ CH═CH₂ Et 205 OC(O)NR′ CH₂CH₂F Et 206 OC(O)NR′ CF₃ Et 207 OC(O)NR″ CH₂CF₃ Et 208 OC(O)NR′ CH₂CN Et 209 OC(O)NR′ cyclopropyl Et 210 OC(O)NR′ cyclopropylmethyl Et 211 OC(O)NR′ CH₂CO₂Me Et 212 OC(O)NR′ CH₂CH₂NMe₂ Et 213 OC(O)NR′ CH₂-(N-morpholinyl) Et 214 OC(O)NR′ 2-chloropyridin-5-yl-methyl Et 215 OC(O)NR′ 2-furanyl Et 216 OC(O)NR′ 2-pyrimidinyl Et 217 OC(O)NR′ 2-oxazolyl Et 218 OC(O)NR′ 5-[1,2,4]-oxadiazolyl Et 219 OC(O)NR′ tetrazolyl Et 220 OC(O)C(O)O H 221 OC(O)C(O)O Me 222 OC(O)C(O)O Et 223 OC(O)C(O)O n-Pr 224 OC(O)C(O)O i-Pr 225 OC(O)C(O)O n-Bu 226 OC(O)C(O)O i-Bu 227 OC(O)C(O)O allyl 228 OC(O)C(O)O CH₂C≡CH 229 OC(O)C(O)O CH═CH₂ 230 OC(O)C(O)O CH₂CH₂F 231 OC(O)C(O)O CF₃ 232 OC(O)C(O)O CH₂CF₃ 234 OC(O)C(O)O CH₂CN 235 OC(O)C(O)O cyclopropyl 236 OC(O)C(O)O cyclopropylmethyl 237 OC(O)C(O)O CH₂CO₂Me 238 OC(O)C(O)O CH₂CH₂NMe₂ 239 OC(O)C(O)O CH₂-(N-morpholinyl) 240 OC(O)C(O)O 2-chloropyridin-5-yl-methyl 241 OC(O)C(O)O 2-furanyl 242 OC(O)C(O)O 2-pyrimidinyl 243 OC(O)C(O)O 2-oxazolyl 244 OC(O)C(O)O 5-[1,2,4]-oxadiazolyl 245 OC(O)C(O)O tetrazolyl 246 S(O)₂NR′ H H 247 S(O)₂NR′ Me H 248 S(O)₂NR′ Et H 249 S(O)₂NR′ n-Pr H 250 S(O)₂NR′ i-Pr H 251 S(O)₂NR′ n-Bu H 252 S(O)₂NR′ i-Bu H 253 S(O)₂NR′ allyl H 254 S(O)₂NR′ CH₂C≡CH H 255 S(O)₂NR′ CH═CH₂ H 256 S(O)₂NR′ CH₂CH₂F H 257 S(O)₂NR′ CF₃ H 258 S(O)₂NR′ CH₂CF₃ H 259 S(O)₂NR′ CH₂CN H 260 S(O)₂NR′ cyclopropyl H 261 S(O)₂NR′ cyclopropylmethyl H 262 S(O)₂NR′ CH₂CO₂Me H 263 S(O)₂NR′ CH₂CH₂NMe₂ H 264 S(O)₂NR′ CH₂-(N-morpholinyl) H 265 S(O)₂NR′ 2-chloropyridin-5-yl-methyl H 266 S(O)₂NR′ 2-furanyl H 267 S(O)₂NR′ 2-pyrimidinyl H 268 S(O)₂NR′ 2-oxazolyl H 269 S(O)₂NR′ 5-[1,2,4]-oxadiazolyl H 270 S(O)₂NR′ tetrazolyl H 271 S(O)₂NR′ H Me 272 S(O)₂NR′ Me Me 273 S(O)₂NR′ Et Me 274 S(O)₂NR′ n-Pr Me 275 S(O)₂NR′ i-Pr Me 276 S(O)₂NR′ n-Bu Me 277 S(O)₂NR′ i-Bu Me 278 S(O)₂NR′ allyl Me 279 S(O)₂NR′ CH₂C≡CH Me 280 S(O)₂NR′ CH═CH₂ Me 281 S(O)₂NR′ CH₂CH₂F Me 282 S(O)₂NR′ CF₃ Me 283 S(O)₂NR′ CH₂CF₃ Me 284 S(O)₂NR′ CH₂CN Me 285 S(O)₂NR′ cyclopropyl Me 286 S(O)₂NR′ cyclopropylmethyl Me 287 S(O)₂NR′ CH₂CO₂Me Me 288 S(O)₂NR′ CH₂CH₂NMe₂ Me 289 S(O)₂NR′ CH₂-(N-morpholinyl) Me 289 S(O)₂NR′ 2-chloropyridin-5-yl-methyl Me 290 S(O)₂NR′ 2-furanyl Me 291 S(O)₂NR′ 2-pyrimidinyl Me 292 S(O)₂NR′ 2-oxazolyl Me 293 S(O)₂NR′ 5-[1,2,4]-oxadiazolyl Me 294 S(O)₂NR′ tetrazolyl Me 295 S(O)₂NR′ H Et 296 S(O)₂NR′ Me Et 297 S(O)₂NR′ Et Et 298 S(O)₂NR′ n-Pr Et 299 S(O)₂NR′ i-Pr Et 300 S(O)₂NR′ n-Bu Et 301 S(O)₂NR′ i-Bu Et 302 S(O)₂NR′ allyl Et 303 S(O)₂NR′ CH₂C≡CH Et 304 S(O)₂NR′ CH═CH₂ Et 305 S(O)₂NR′ CH₂CH₂F Et 306 S(O)₂NR′ CF₃ Et 307 S(O)₂NR′ CH₂CF₃ Et 308 S(O)₂NR′ CH₂CN Et 309 S(O)₂NR′ cyclopropyl Et 310 S(O)₂NR′ cyclopropylmethyl Et 311 S(O)₂NR′ CH₂CO₂Me Et 312 S(O)₂NR′ CH₂CH₂NMe₂ Et 313 S(O)₂NR′ CH₂-(N-morpholinyl) Et 314 S(O)₂NR′ 2-chloropyridin-5-yl-methyl Et 315 S(O)₂NR′ 2-furanyl Et 316 S(O)₂NR′ 2-pyrimidinyl Et 317 S(O)₂NR′ 2-oxazolyl Et 318 S(O)₂NR′ 5-[1,2,4]-oxadiazolyl Et 319 S(O)₂NR′ tetrazolyl Et

TABLE 2

Ex. m.p. No. Y R R′ [° C.]  1 O H 128  2 O Et oil  3 O n-Pr  4 O i-Pr oil  5 O n-Bu oil  6 O i-Bu oil  7 O allyl oil  8 O CH₂C≡CH oil  9 O CH═CH₂  10 O CH₂CH₂F  11 O CF₃  12 O CH₂CF₃ oil  13 O CH₂CN  14 O cyclopropyl  15 O cyclopropylmethyl oil  16 O CH₂CO₂Me  17 O CH₂CH₂NMe₂  18 O CH₂-(N-morpholinyl) oil  19 O 2-chloropyridin-5-yl-methyl  20 O 2-furanyl  21 O 2-pyrimidinyl  22 O 2-oxazolyl  23 O 5-[1,2,4]-oxindazolyl  24 O tetrazolyl  25 O 1,3-oxindol-2-yl oil  26 O CH₂CH₂OMe oil  27 O CH₂CH₂OCH₂CH₂OMe oil  28 O CH₂CH₂SCH₂CH₃ oil  29 S H  30 S Et oil  31 S n-Pr oil  32 S i-Pr  33 S n-Bu  34 S i-Bu oil  35 S allyl oil  36 S CH₂C≡CH  37 S CH═CH₂  38 S CH₂CH₂F  39 S CF₃ oil  40 S CH₂CF₃ oil  41 S CH₂CN  42 S cyclopropyl  43 S cyclopropylmethyl  44 S CH₂CO₂Me oil  45 S CH₂CO₂Et oil  46 S CH₂CH₂CO₂Me oil  47 S CH₂CH₂NMe₂  48 S CH₂-(N-morpholinyl)  49 S 2-chloropyridin-5-yl-methyl  50 S 2-furanyl  51 S 2-pyridinyl oil  52 S 2-pyrimidinyl crystal- line  53 S 2-oxazolyl  54 S 5-[1,2,4]-oxadiazolyl  55 S tetrazolyl  56 S CH₂CH₂OH oil  57 S Ac oil  58 S

 59 NR′(CO)

136  60 NR′C(O)O CMe₃ H Öl  61 NR′

CO₂allyl Öl  62 NR′SO₂ C(H)Cl₂ Me Öl  63 NR′SO₂ Bu Me Öl  64 NR′SO₂ Pr Me Öl  65 S N-Me-imidazol-2-yl solid  66 S [1,2,4]-triazol-3-yl solid  67 S 4-Me-[1,2,4]-triazol-3-yl crystal- line  68 S 4-Me-tetrazol-5-yl solid  69 S 2-thiazolin-2-yl crystal- line  70 S cyclohexyl wax  71 S(O) Et  72 S(O) n-Pr  73 S(O) i-Pr oil  74 S(O) n-Bu  75 S(O) i-Bu  76 S(O) allyl  77 S(O) CH₂C≡CH  78 S(O) CH═CH₂  79 S(O) CH₂CH₂F  80 S(O) CF₃ solid CH₂CF₃  81 S(O) CH₂CN 129  82 S(O) cyclopropyl  83 S(O) cyclopropylmethyl  84 S(O) CH₂CO₂Me  85 S(O) CH₂CH₂NMe₂  86 S(O) CH₂-(N-morpholinyl)  87 S(O) 2-chloropyridin-5-yl-methyl  88 S(O) 2-furanyl  89 S(O) 2-pyrimidinyl  90 S(O) 2-oxazolyl  91 S(O) 5-[1,2,4]-oxadiazolyl  92 S(O) tetrazolyl  93 S(O)  94 S(O)₂ Me  92  95 S(O)₂ Et  96 S(O)₂ n-Pr  73  97 S(O)₂ i-Pr 109  98 S(O)₂ n-Bu  99 S(O)₂ n-Hex  87 100 S(O)₂ i-Bu 101 S(O)₂ allyl 102 S(O)₂ CH₂C≡CH 103 S(O)₂ CH═CH₂ 104 S(O)₂ CH₂CH₂F 105 S(O)₂ CF₃ 106 S(O)₂ CH₂CF₃ crystal- line 107 S(O)₂ CH₂CN 108 S(O)₂ cyclopropyl 109 S(O)₂ cyclopropylmethyl 110 S(O)₂ CH₂CO₂Me 111 S(O)₂ CH₂CH₂NMe₂ 112 S(O)₂ CH₂-(N-morpholinyl) 113 S(O)₂ 2-chloropyridin-5-yl-methyl 114 S(O)₂ 2-furanyl 115 S(O)₂ 2-furfuryl  99 116 S(O)₂ 2-thienyl 100 117 S(O)₂ 2-pyrimidinyl 118 S(O)₂ 2-oxazolyl 119 S(O)₂ 5-[1,2,4]-oxadiazolyl 120 S(O)₂ tetrazolyl 121 S(O)₂ ONa 214 122 S(O)₂ p-F-benzyl 156 123 OC(O) H 124 OC(O) Me 125 OC(O) Et oil 126 OC(O) n-Pr 127 OC(O) i-Pr 128 OC(O) n-Bu 129 OC(O) i-Bu oil 130 OC(O) t-Bu oil 131 OC(O) allyl 132 OC(O) CH₂C≡CH 133 OC(O) CH═CH₂ oil 134 OC(O) CH₂CH₂F 135 OC(O) CF₃ 136 OC(O) CH₂CF₃ 137 OC(O) CH₂CH₂SiMe₃ oil 138 OC(O) CH₂CN oil 139 OC(O) cyclopropyl 140 OC(O) cyclopropylmethyl 141 OC(O) CH₂CO₂Me oil 142 OC(O) CH₂CH₂NMe₂ 143 OC(O) CH₂OMe 144 OC(O) CH₂-(N-morpholinyl) 145 OC(O) 2-chloropyridin-5-yl-methyl 146 OC(O) 2-furanyl 147 OC(O) 2-pyrimidinyl 148 OC(O) 2-oxazolyl 149 OC(O) 5-[1,2,4]-oxadiazolyl 150 OC(O) tetrazolyl 151 OC(O) 2-oxopyrrolidin-5-yl oil 152 OC(O)O H 153 OC(O)O Me oil 154 OC(O)O Et oil 155 OC(O)O n-Pr oil 156 OC(O)O i-Pr 157 OC(O)O n-Bu 158 OC(O)O i-Bu 159 OC(O)O allyl 160 OC(O)O CH₂C≡CH 161 OC(O)O CH═CH₂ 162 OC(O)O CH₂CH₂F 163 OC(O)O CF₃ 164 OC(O)O CH₂CF₃ 165 OC(O)O CH₂CN 166 OC(O)O cyclopropyl 167 OC(O)O cyclopropylmethyl 168 OC(O)O CH₂CO₂Me 169 OC(O)O CH₂CH₂NMe₂ 170 OC(O)O CH₂-(N-morpholinyl) 171 OC(O)O 2-chloropyridin-5-yl-methyl 172 OC(O)O 2-furanyl 173 OC(O)O 2-pyrimidinyl 174 OC(O)O 2-oxazolyl 175 OC(O)O 5-[1,2,4]-oxadiazolyl 176 OC(O)O tetrazolyl 177 OC(O)NR′ H H 178 OC(O)NR′ Me H 179 OC(O)NR′ Et H 180 OC(O)NR′ n-Pr H 181 OC(O)NR′ i-Pr H 182 OC(O)NR′ n-Bu H 183 OC(O)NR′ i-Bu H 184 OC(O)NR′ allyl H 185 OC(O)NR′ CH₂C≡CH H 186 OC(O)NR′ CH═CH₂ H 187 OC(O)NR′ CH₂CH₂F H 188 OC(O)NR′ CF₃ H 189 OC(O)NR′ CH₂CF₃ H 190 OC(O)NR′ CH₂CN H 191 OC(O)NR′ cyclopropyl H 192 OC(O)NR′ cyclopropylmethyl H 193 OC(O)NR′ CH₂CO₂Me H 194 OC(O)NR′ CH₂CH₂NMe₂ H 195 OC(O)NR′ CH₂-(N-morpholinyl) H 196 OC(O)NR′ 2-chloropyridin-5-yl-methyl H 197 OC(O)NR′ 2-furanyl H 198 OC(O)NR′ 2-pyrimidinyl H 199 OC(O)NR′ 2-oxazolyl H 200 OC(O)NR′ 5-[1,2,4]-oxadiazolyl H 201 OC(O)NR′ tetrazolyl H 202 OC(O)NR′ H Me 203 OC(O)NR′ Me Me oil 204 OC(O)NR′ Et Me 205 OC(O)NR′ n-Pr Me 206 OC(O)NR′ i-Pr Me 207 OC(O)NR′ n-Bu Me 208 OC(O)NR′ i-Bu Me 209 OC(O)NR′ allyl Me 210 OC(O)NR′ CH₂C≡CH Me 211 OC(O)NR′ CH═CH₂ Me 212 OC(O)NR′ CH₂CH₂F Me 213 OC(O)NR′ CF₃ Me 214 OC(O)NR′ CH₂CF₃ Me 215 OC(O)NR′ CH₂CN Me 216 OC(O)NR′ cyclopropyl Me 217 OC(O)NR′ cyclopropylmethyl Me 218 OC(O)NR′ CH₂CO₂Me Me 219 OC(O)NR′ CH₂CH₂NMe₂ Me 220 OC(O)NR′ CH₂-(N-morpholinyl) Me 221 OC(O)NR′ 2-chloropyridin-5-yl-methyl Me 222 OC(O)NR′ 2-furanyl Me 223 OC(O)NR′ 2-pyrimidinyl Me 224 OC(O)NR′ 2-oxazolyl Me 225 OC(O)NR′ 5-[1,2,4]-oxadiazolyl Me 226 OC(O)NR′ tetrazolyl Me 227 OC(O)NR′ n-Hex Me 228 OC(O)NR′ H Et 229 OC(O)NR′ Me Et 230 OC(O)NR′ Et Et 231 OC(O)NR′ n-Pr Et 232 OC(O)NR′ i-Pr Et 233 OC(O)NR′ n-Bu Et 234 OC(O)NR′ i-Bu Et 235 OC(O)NR′ allyl Et 236 OC(O)NR′ CH₂C≡CH Et 237 OC(O)NR′ CH═CH₂ Et 238 OC(O)NR′ CH₂CH₂F Et 239 OC(O)NR′ CF₃ Et 240 OC(O)NR′ CH₂CF₃ Et 241 OC(O)NR′ CH₂CN Et 242 OC(O)NR′ cyclopropyl Et 243 OC(O)NR′ cyclopropylmethyl Et 244 OC(O)NR′ CH₂CO₂Me Et 245 OC(O)NR′ CH₂CH₂NMe₂ Et 246 OC(O)NR′ CH₂-(N-morpholinyl) Et 247 OC(O)NR′ 2-chloropyridin-5-yl-methyl Et 248 OC(O)NR′ 2-furanyl Et 249 OC(O)NR′ 2-pyrimidinyl Et 250 OC(O)NR′ 2-oxazolyl Et 251 OC(O)NR′ 5-[1,2,4]-oxadiazolyl Et 252 OC(O)NR′ tetrazolyl Et 253 OC(O)NR′ H Et 254 OC(O)C(O)O H 255 OC(O)C(O)O Me oil 256 OC(O)C(O)O Et oil 257 OC(O)C(O)O n-Pr 258 OC(O)C(O)O i-Pr 259 OC(O)C(O)O n-Bu 260 OC(O)C(O)O i-Bu 261 OC(O)C(O)O allyl 262 OC(O)C(O)O CH₂C≡CH 263 OC(O)C(O)O CH═CH₂ 264 OC(O)C(O)O CH₂CH₂F 265 OC(O)C(O)O CF₃ 266 OC(O)C(O)O CH₂CF₃ 267 OC(O)C(O)O CH₂CN 268 OC(O)C(O)O cyclopropyl 269 OC(O)C(O)O cyclopropylmethyl 270 OC(O)C(O)O CH₂CO₂Me 271 OC(O)C(O)O CH₂CH₂NMe₂ 272 OC(O)C(O)O CH₂-(N-morpholinyl) 273 OC(O)C(O)O 2-chloropyridin-5-yl-methyl 274 OC(O)C(O)O 2-furanyl 275 OC(O)C(O)O 2-pyrimidinyl 276 OC(O)C(O)O 2-oxazolyl 277 OC(O)C(O)O 5-[1,2,4]-oxadiazolyl 278 OC(O)C(O)O tetrazolyl 279 S(O)₂NR′ H H 280 S(O)₂NR′ Me H 281 S(O)₂NR′ Et H 282 S(O)₂NR′ n-Pr H 283 S(O)₂NR′ i-Pr H  93 284 S(O)₂NR′ n-Bu H 285 S(O)₂NR′ i-Bu H 286 S(O)₂NR′ allyl H  83 287 S(O)₂NR′ CH₂C≡CH H 288 S(O)₂NR′ CH═CH₂ H 289 S(O)₂NR′ CH₂CH₂F H 290 S(O)₂NR′ CF₃ H 291 S(O)₂NR′ CH₂CF₃ H 292 S(O)₂NR′ CH₂CN H 293 S(O)₂NR′ cyclopropyl H 294 S(O)₂NR′ cyclopropylmethyl H solid 295 S(O)₂NR′ CH₂CO₂Me H 296 S(O)₂NR′ CH₂CH₂NMe₂ H 297 S(O)₂NR′ CH₂-(N-morpholinyl) H 298 S(O)₂NR′ 2-chloropyridin-5-yl-methyl H 299 S(O)₂NR′ 2-furanyl H 300 S(O)₂NR′ 2-pyrimidinyl H 301 S(O)₂NR′ 2-oxazolyl H 302 S(O)₂NR′ 5-[1,2,4]-oxadiazolyl H 303 S(O)₂NR′ tetrazolyl H 304 S(O)₂NR′ H Me 305 S(O)₂NR′ Me Me 306 S(O)₂NR′ Et Me oil 307 S(O)₂NR′ n-Pr Me 308 S(O)₂NR′ i-Pr Me oil 309 S(O)₂NR′ n-Bu Me 310 S(O)₂NR′ i-Bu Me 311 S(O)₂NR′ allyl Me 312 S(O)₂NR′ CH₂C≡CH Me  94 313 S(O)₂NR′ CH═CH₂ Me 314 S(O)₂NR′ CH₂CH₂F Me 315 S(O)₂NR′ CF₃ Me 316 S(O)₂NR′ CH₂CF₃ Me 317 S(O)₂NR′ CH₂CN Me 318 S(O)₂NR′ cyclopropyl Me 319 S(O)₂NR′ cyclopropylmethyl Me 320 S(O)₂NR′ CH₂CO₂Me Me 321 S(O)₂NR′ CH₂CH₂NMe₂ Me 322 S(O)₂NR′ CH₂-(N-morpholinyl) Me 323 S(O)₂NR′ 2-chloropyridin-5-yl-methyl Me 324 S(O)₂NR′ furanyl Me 325 S(O)₂NR′ 2-pyrimidinyl Me 326 S(O)₂NR′ 2-oxazolyl Me 327 S(O)₂NR′ 5-[1,2,4]-oxadiazolyl Me 328 S(O)₂NR′ tetrazolyl Me 329 S(O)₂NR′ H Et 330 S(O)₂NR′ Me Et 331 S(O)₂NR′ Et Et 332 S(O)₂NR′ n-Pr Et 333 S(O)₂NR′ i-Pr Et  70 334 S(O)₂NR′ n-Bu Et 335 S(O)₂NR′ i-Bu Et 336 S(O)₂NR′ allyl Et oil 337 S(O)₂NR′ CH₂C≡CH Et 338 S(O)₂NR′ CH═CH₂ Et 339 S(O)₂NR′ CH₂CH₂F Et 340 S(O)₂NR′ CF₃ Et 341 S(O)₂NR′ CH₂CF₃ Et 342 S(O)₂NR′ CH₂CN Et 343 S(O)₂NR′ cyclopropyl Et 344 S(O)₂NR′ cyclopropylmethyl Et 345 S(O)₂NR′ CH₂CO₂Me Et 346 S(O)₂NR′ CH₂CH₂NMe₂ Et 347 S(O)₂NR′ CH₂-(N-morpholinyl) Et 348 S(O)₂NR′ 2-chloropyridin-5-yl-methyl Et 349 S(O)₂NR′ furanyl Et 350 S(O)₂NR′ 2-pyrimidinyl Et 351 S(O)₂NR′ 2-oxazolyl Et 352 S(O)₂NR′ 5-[1,2,4]-oxadiazolyl Et 353 S(O)₂NR′ tetrazolyl Et 354 S(O)₂NR′ n-Pr n-Pr oil 355 S(O)₂NR′ CH₂SCH₂CH₂ n-Pr 356 S(O)₂NR′ CH₂CH₂CH₂CH₂CH₂ n-Pr 152 357 S(O)₂NR′ CH₂CH═CHCH₂CH₂ n-Pr 138 358 S 2-methylmercapto-1,3,4-thiadiazol-5-yl  92 359 S 5-(trifluoromethyl)-pyridin-2-yl  78 360 S 3-(trifluoromethyl)-pyridin-2-yl  68 361 S 4-methylthiazol-2-yl oil 362 S 3-(methylmercapto)-1,2,4-thiadiazol- oil 5-yl 363 S 4-pyridinyl  88 364 S 2-methylfuran-3-yl oil 365 S 4-(trifluoromethoxy)-phenyl  57 366 S 2-imidazolyl 171 367 S 5-methyl-1,2,4-triazol-3-yl  95 368 S 2-thiazolyl oil 369 S dimethylaminothiocarbonyl solid 370 S 4,6-dimethylpyrimidin-2-yl oil 371 S 5-methyl-1,3,4-thiadiazol-2-yl  98 372 NR′C(S)NH CO₂Et H 136 373 NR′C(O) CH(imidazolyl-)CF₂C(O) oil 374 NR′C(O) CH(Me)CH₂C(O) oil 375 NR′C(O) CMe₂CH₂C(O) oil 376 NR′C(O) CH(Me)CH(Me)C(O) oil 377 NR′C(O) CH₂CH₂CH₂C(O) oil 378 NR′C(O) CH(Me)CH₂CH₂C(O) oil 379 NR′C(O) CH₂CH(Me)CH₂C(O) oil 380 NR′C(O) CH₂CMe₂CH₂C(O) oil 381 NR′C(O) CH₂C [—(CH₂)₄—]CH₂C(O) oil 382 NR′C(O)

192 383 NR′C(O)N(H) CH(CHMe₂)CO₂Et H oil 384 NR′C(S)N(H) Et H oil 385 NR′C(S)N(H) CMe₃ H 113 386 NR′C(S)N(H) -p-Tol H oil 387 NR′C(O)

H 148 388 NR′C(O)N(H) Et H 144 389 NR′C(O)N(H) C(H)Me₂ H 159 390 NR′C(O)N(H) Bu H 117 391 NR′C(O)N(H) (CH₂)₄Me H 118 392 NR′C(O)N(H) cyclohexyl H 160 393 NR′C(O)N(H) C(H)MeCO₂Et H 157 394 NR′C(O)N(H) C(O)Ph H 182 395 NR′C(O)N(H) (4-CF₃-Ph) H 170 396 NR′C(O)N(H) (2,6-C₆H₃F₂) H 193 397 NR′C(O)

oil 398 NR′C(O) CH₂C(H)PhCH₂C(O) oil 399 NR′C(O) CMe═CMeC(O) oil 400 NR′C(O)

oil 401 NR′(CO)N(H) CMe₃ H 120 402 NR′C(O)O CH₂C≡CH H solid 403 NR′SO₂ C(H)Me₂ H oil 404 NR′C(O) CH₂OC(O)Me H  80 405 NR′C(O) (CH₂)₃Cl H  56 406 NR′C(O) (CH₂)₂SMe H  96 407 NR′C(O)O Bu H oil 408 NR′C(O)O cyclopentyl H oil 409 NR′C(O) CH₂CH₂C(O)  87 410 NR′C(O)N(H) Ph H 129 411 NR′H⁺HSO₄ ⁻ H H solid

TABLE 3

Ex. m.p. No. Y R R′ [° C.]  1 O n-Pr oil  2 O i-Pr oil  3 O n-Bu  4 O i-Bu  5 O allyl oil  6 O CH₂C≡CH oil  7 O CH═CH₂  8 O CH₂CH₂F  9 O CF₃  10 O CH₂CF₃  11 O CH₂CN  12 O cyclopropyl  13 O cyclopropylmethyl  14 O CH₂CO₂Me  15 O CH₂CH₂NMe₂  16 O CH₂-(N-morpholinyl)  17 O 2-chloropyridin-5-yl-methyl  18 O n-Hex  19 O 2-furanyl  20 O 2-pyrimidinyl  21 O 2-oxazolyl  22 O 5-[1,2,4]-oxadiazolyl  23 O tetrazolyl  24 O 2-hexahydropropanyl  25 S H  26 S Et  27 S i-Pr oil  28 S n-Bu  29 S i-Bu  30 S allyl  31 S CH₂C≡CH  32 S CH═CH₂  33 S CH₂CH₂F  34 S CF₃  35 S CH₂CF₃ oil  36 S CH₂CN  37 S cyclopropyl  38 S cyclopropylmethyl  39 S CH₂CO₂Me  40 S CH₂CH₂NMe₂  41 S CH₂-(N-morpholinyl)  42 S 2-chloropyridin-5-yl-methyl  43 S n-Hex  44 S 2-furanyl  45 S 2-pyrimidinyl  46 S 2-oxazolyl  47 S 5-[1,2,4]-oxadiazolyl  48 tetrazolyl  49 S

oil  50 S(O) Me  51 S(O) Et  52 S(O) n-Pr  53 S(O) i-Pr  54 S(O) n-Bu  55 S(O) i-Bu  56 S(O) allyl  57 S(O) CH₂C≡CH  58 S(O) CH═CH₂  59 S(O) CH₂CH₂F  60 S(O) CF₃  61 S(O) CH₂CF₃  62 S(O) CH₂CN  63 S(O) cyclopropyl  64 S(O) cyclopropylmethyl  65 S(O) CH₂CO₂Me  66 S(O) CH₂CH₂NMe₂  67 S(O) CH₂-(N-morpholinyl)  68 S(O) 2-chloropyridin-5-yl-methyl  69 S(O) n-Hex  70 S(O) 2-furanyl  71 S(O) 2-pyrimidinyl  72 S(O) 2-oxazolyl  73 S(O) 5-[1,2,4]-oxadiazolyl  74 S(O) tetrazolyl  75 S(O)₂ Me  84  76 S(O)₂ Et  77 S(O)₂ n-Pr  78 S(O)₂ i-Pr  79 S(O)₂ n-Bu  80 S(O)₂ i-Bu  81 S(O)₂ allyl  82 S(O)₂ CH₂C≡CH  83 S(O)₂ CH═CH₂  84 S(O)₂ CH₂CH₂F  85 S(O)₂ CF₃  86 S(O)₂ CH₂CF₃  87 S(O)₂ CH₂CN  88 S(O)₂ cyclopropyl  89 S(O)₂ cyclopropylmethyl  90 S(O)₂ CH₂CO₂Me  91 S(O)₂ CH₂CH₂NMe₂  92 S(O)₂ CH₂-(N-morpholinyl)  93 S(O)₂ 2-chloropyridin-5-yl-methyl  94 S(O)₂ n-Hex  95 S(O)₂ furanyl  96 S(O)₂ 2-pyrimidinyl  97 S(O)₂ 2-oxazolyl  98 S(O)₂ 5-[1,2,4]-oxadiazolyl  99 S(O)₂ tetrazolyl 100 OC(O) H 101 OC(O) Et 102 OC(O) n-Pr 103 OC(O) i-Pr 104 OC(O) n-Bu 105 OC(O) i-Bu 106 OC(O) allyl 107 OC(O) CH₂C≡CH 108 OC(O) CH═CH₂ 109 OC(O) CH₂CH₂F 110 OC(O) CF₃ 111 OC(O) CH₂CF₃ 112 OC(O) CH₂CN 113 OC(O) cyclopropyl 114 OC(O) cyclopropylmethyl 115 OC(O) CH₂CO₂Me 116 OC(O) CH₂CH₂NMe₂ 117 OC(O) CH₂-(N-morpholinyl) 118 OC(O) 2-chloropyridin-5-yl-methyl 119 OC(O) n-Hex 120 OC(O) 2-furanyl 121 OC(O) 2-pyrimidinyl 122 OC(O) 2-oxazolyl 123 OC(O) 5-[1,2,4]-oxadiazolyl 124 OC(O) tetrazolyl 125 OC(O)O Me 126 OC(O)O Et 127 OC(O)O n-Pr 128 OC(O)O i-Pr 129 OC(O)O n-Bu 130 OC(O)O i-Bu 131 OC(O)O allyl 132 OC(O)O CH₂C≡CH 133 OC(O)O CH═CH₂ 134 OC(O)O CH₂CH₂F 135 OC(O)O CF₃ 136 OC(O)O CH₂CF₃ 137 OC(O)O CH₂CN 138 OC(O)O cyclopropyl 139 OC(O)O cyclopropylmethyl 140 OC(O)O CH₂CO₂Me 141 OC(O)O CH₂CH₂NMe₂ 142 OC(O)O CH₂-(N-morpholinyl) 143 OC(O)O 2-chloropyridin-5-yl-methyl 144 OC(O)O n-Hex 145 OC(O)O 2-furanyl 146 OC(O)O 2-pyrimidinyl 147 OC(O)O 2-oxazolyl 148 OC(O)O 5-[1,2,4]-oxadiazolyl 149 OC(O)O tetrazolyl 150 OC(O)NR′ H H 151 OC(O)NR′ Me H 152 OC(O)NR′ Et H 154 OC(O)NR′ n-Pr H 155 OC(O)NR′ i-Pr H 156 OC(O)NR′ n-Bu H 157 OC(O)NR′ i-Bu H 158 OC(O)NR′ allyl H 159 OC(O)NR′ CH₂C≡CH H 160 OC(O)NR′ CH═CH₂ H 161 OC(O)NR′ CH₂CH₂F H 162 OC(O)NR′ CF₃ H 163 OC(O)NR′ CH₂CF₃ H 164 OC(O)NR′ CH₂CN H 165 OC(O)NR′ cyclopropyl H 166 OC(O)NR′ cyclopropylmethyl H 167 OC(O)NR′ CH₂CO₂Me H 168 OC(O)NR′ CH₂CH₂NMe₂ H 169 OC(O)NR′ CH₂-(N-morpholinyl) H 170 OC(O)NR′ 2-chloropyridin-5-yl-methyl H 171 OC(O)NR′ n-Hex H 172 OC(O)NR′ 2-furanyl H 173 OC(O)NR′ 2-pyrimidinyl H 174 OC(O)NR′ 2-oxazolyl H 175 OC(O)NR′ 5-[1,2,4]-oxadiazolyl H 176 OC(O)NR′ tetrazolyl H 177 OC(O)NR′ H Me 178 OC(O)NR′ Me Me 179 OC(O)NR′ Et Me 180 OC(O)NR′ n-Pr Me 181 OC(O)NR′ i-Pr Me 182 OC(O)NR′ n-Bu Me 183 OC(O)NR′ i-Bu Me 184 OC(O)NR′ allyl Me 185 OC(O)NR′ CH₂C≡CH Me 186 OC(O)NR′ CH═CH₂ Me 187 OC(O)NR′ CH₂CH₂F Me 188 OC(O)NR′ CF₃ Me 189 OC(O)NR′ CH₂CF₃ Me 190 OC(O)NR′ CH₂CN Me 191 OC(O)NR′ cyclopropyl Me 192 OC(O)NR′ cyclopropylmethyl Me 193 OC(O)NR′ CH₂CO₂Me Me 194 OC(O)NR′ CH₂CH₂NMe₂ Me 195 OC(O)NR′ CH₂-(N-morpholinyl) Me 196 OC(O)NR′ 2-chloropyridin-5-yl-methyl Me 197 OC(O)NR′ n-Hex Me 198 OC(O)NR′ 2-furanyl Me 199 OC(O)NR′ 2-pyrimidinyl Me 200 OC(O)NR′ 2-oxazolyl Me 201 OC(O)NR′ 5-[1,2,4]-oxadiazolyl Me 202 OC(O)NR′ tetrazolyl Me 203 OC(O)NR′ H Et 204 OC(O)NR′ Me Et 205 OC(O)NR′ Et Et 206 OC(O)NR′ n-Pr Et 207 OC(O)NR′ i-Pr Et 208 OC(O)NR′ n-Bu Et 209 OC(O)NR′ i-Bu Et 210 OC(O)NR′ allyl Et 211 OC(O)NR′ CH₂C≡CH Et 212 OC(O)NR′ CH═CH₂ Et 213 OC(O)NR′ CH₂CH₂F Et 214 OC(O)NR′ CF₃ Et 215 OC(O)NR′ CH₂CF₃ Et 216 OC(O)NR′ CH₂CN Et 217 OC(O)NR′ cyclopropyl Et 218 OC(O)NR′ cyclopropylmethyl Et 219 OC(O)NR′ CH₂CO₂Me Et 220 OC(O)NR′ CH₂CH₂NMe₂ Et 221 OC(O)NR′ CH₂-(N-morpholinyl) Et 222 OC(O)NR′ 2-chloropyridin-5-yl-methyl Et 223 OC(O)NR′ n-Hex Et 224 OC(O)NR′ 2-furanyl Et 225 OC(O)NR′ 2-pyrimidinyl Et 226 OC(O)NR′ 2-oxazolyl Et 227 OC(O)NR′ 5-[1,2,4]-oxadiazolyl Et 228 OC(O)NR′ tetrazolyl Et 229 OC(O)C(O)O H 230 OC(O)C(O)O Me 231 OC(O)C(O)O Et 232 OC(O)C(O)O n-Pr 233 OC(O)C(O)O i-Pr 234 OC(O)C(O)O n-Bu 235 OC(O)C(O)O i-Bu 236 OC(O)C(O)O allyl 237 OC(O)C(O)O CH₂C≡CH 238 OC(O)C(O)O CH═CH₂ 239 OC(O)C(O)O CH₂CH₂F 240 OC(O)C(O)O CF₃ 241 OC(O)C(O)O CH₂CF₃ 242 OC(O)C(O)O CH₂CN 243 OC(O)C(O)O cyclopropyl 244 OC(O)C(O)O cyclopropylmethyl 245 OC(O)C(O)O CH₂CO₂Me 246 OC(O)C(O)O CH₂CH₂NMe₂ 247 OC(O)C(O)O CH₂-(N-morpholinyl) 248 OC(O)C(O)O 2-chloropyridin-5-yl-methyl 249 OC(O)C(O)O n-Hex 250 OC(O)C(O)O furanyl 251 OC(O)C(O)O 2-pyrimidinyl 252 OC(O)C(O)O 2-oxazolyl 253 OC(O)C(O)O 5-[1,2,4]-oxadiazolyl 254 OC(O)C(O)O tetrazolyl 255 S(O)₂NR′ H H 256 S(O)₂NR′ Me H 257 S(O)₂NR′ Et H 258 S(O)₂NR′ n-Pr H 259 S(O)₂NR′ i-Pr H 260 S(O)₂NR′ n-Bu H 261 S(O)₂NR′ i-Bu H 262 S(O)₂NR′ allyl H 263 S(O)₂NR′ CH₂C≡CH H 264 S(O)₂NR′ CH═CH₂ H 265 S(O)₂NR′ CH₂CH₂F H 266 S(O)₂NR′ CF₃ H 267 S(O)₂NR′ CH₂CF₃ H 268 S(O)₂NR′ CH₂CN H 269 S(O)₂NR′ cyclopropyl H 270 S(O)₂NR′ cyclopropylmethyl H 271 S(O)₂NR′ CH₂CO₂Me H 272 S(O)₂NR′ CH₂CH₂NMe₂ H 273 S(O)₂NR′ CH₂-(N-morpholinyl) H 274 S(O)₂NR′ 2-chloropyridin-5-yl-methyl H 275 S(O)₂NR′ n-Hex H 276 S(O)₂NR′ furanyl H 277 S(O)₂NR′ 2-pyrimidinyl H 278 S(O)₂NR′ 2-oxazolyl H 279 S(O)₂NR′ 5-[1,2,4]-oxadiazolyl 280 S(O)₂NR′ tetrazolyl 281 S(O)₂NR′ H Me 282 S(O)₂NR′ Me Me 283 S(O)₂NR′ Et Me 284 S(O)₂NR′ n-Pr Me 285 S(O)₂NR′ i-Pr Me 286 S(O)₂NR′ n-Bu Me 287 S(O)₂NR′ i-Bu Me 288 S(O)₂NR′ allyl Me 289 S(O)₂NR′ CH₂C≡CH Me 290 S(O)₂NR′ CH═CH₂ Me 291 S(O)₂NR′ CH₂CH₂F Me 292 S(O)₂NR′ CF₃ Me 293 S(O)₂NR′ CH₂CF₃ Me 294 S(O)₂NR′ CH₂CN Me 295 S(O)₂NR′ cyclopropyl Me 296 S(O)₂NR′ cyclopropylmethyl Me 297 S(O)₂NR′ CH₂CO₂Me Me 298 S(O)₂NR′ CH₂CH₂NMe₂ Me 299 S(O)₂NR′ CH₂-(N-morpholinyl) Me 300 S(O)₂NR′ 2-chloropyridin-5-yl-methyl Me 301 S(O)₂NR′ n-Hex Me 302 S(O)₂NR′ furanyl Me 303 S(O)₂NR′ 2-pyrimidinyl Me 304 S(O)₂NR′ 2-oxazolyl Me 305 S(O)₂NR′ 5-[1,2,4]-oxadiazolyl Me 306 S(O)₂NR′ tetrazolyl Me 307 S(O)₂NR′ H Et 308 S(O)₂NR′ Me Et 309 S(O)₂NR′ Et Et 310 S(O)₂NR′ n-Pr Et 311 S(O)₂NR′ i-Pr Et 312 S(O)₂NR′ n-Bu Et 313 S(O)₂NR′ i-Bu Et 314 S(O)₂NR′ allyl Et 315 S(O)₂NR′ CH₂C≡CH Et 316 S(O)₂NR′ CH═CH₂ Et 317 S(O)₂NR′ CH₂CH₂F Et 318 S(O)₂NR′ CF₃ Et 319 S(O)₂NR′ CH₂CF₃ Et 320 S(O)₂NR′ CH₂CN Et 321 S(O)₂NR′ cyclopropyl Et 322 S(O)₂NR′ cyclopropylmethyl Et 323 S(O)₂NR′ CH₂CO₂Me Et 324 S(O)₂NR′ CH₂CH₂NMe₂ Et 325 S(O)₂NR′ CH₂-(N-morpholinyl) Et 326 S(O)₂NR′ 2-chloropyridin-5-yl-methyl Et 327 S(O)₂NR′ n-Hex Et 328 S(O)₂NR′ furanyl Et 329 S(O)₂NR′ n-Hex Et 330 S(O)₂NR′ 2-pyrimidinyl Et 331 S(O)₂NR′ 2-oxazolyl Et 332 S(O)₂NR′ 5-[1,2,4]-oxadiazolyl Et 333 S(O)₂NR′ tetrazolyl Et

TABLE 4

Ex. m.p. No. Y R R′ [° C.]  1 O H  2 O Me  3 O Et oil  4 O n-Pr  5 O i-Pr  6 O n-Bu  7 O i-Bu  8 O allyl  9 O CH₂C≡CH  10 O CH═CH₂  11 O CH₂CH₂F  12 O CF₃  13 O CH₂CF₃  14 O CH₂CN  15 O cyclopropyl  16 O cyclopropylmethyl  17 O CH₂CO₂Me  18 O CH₂CH₂NMe₂  19 O CH₂-(N-morpholinyl)  20 O 2-chloropyridin-5-yl-methyl  21 O n-Hex  22 O 2-furanyl  23 O 2-pyrimidinyl  24 O 2-oxazolyl  25 O 5-[1,2,4]-oxadiazolyl  26 O tetrazolyl  27 S H  28 S Me  29 S Et  30 S n-Pr  31 S i-Pr  32 S n-Bu  33 S i-Bu  34 S allyl  35 S CH₂C≡CH  36 S CH═CH₂  37 S CH₂CH₂F  38 S CF₃  39 S CH₂CF₃  40 S CH₂CN  41 S cyclopropyl  42 S cyclopropylmethyl  43 S CH₂CO₂Me  44 S CH₂CH₂NMe₂  45 S CH₂-(N-morpholinyl)  46 S 2-chloropyridin-5-yl-methyl  47 S n-Hex  48 S 2-furanyl  49 S 2-pyrimidinyl  50 S 2-oxazolyl  51 S 5-[1,2,4]-oxadiazolyl  52 S tetrazolyl  53 S(O) H  54 S(O) Me  55 S(O) Et  56 S(O) n-Pr  57 S(O) i-Pr  58 S(O) n-Bu  59 S(O) i-Bu  60 S(O) allyl  61 S(O) CH₂C═CH  62 S(O) CH═CH₂  63 S(O) CH₂CH₂F  64 S(O) CF₃  65 S(O) CH₂CF₃  66 S(O) CH₂CN  67 S(O) cyclopropyl  68 S(O) cyclopropylmethyl  69 S(O) CH₂CO₂Me  70 S(O) CH₂CH₂NMe₂  71 S(O) CH₂-(N-morpholinyl)  72 S(O) 2-chloropyridin-5-yl-methyl  73 S(O) n-Hex  74 S(O) 2-furanyl  75 S(O) 2-pyrimidinyl  76 S(O) 2-oxazolyl  77 S(O) 5-[1,2,4]-oxadiazolyl  78 S(O) tetrazolyl  79 S(O)₂ n-Hex  80 S(O)₂ Me  81 S(O)₂ Et  82 S(O)₂ n-Pr  83 S(O)₂ i-Pr  84 S(O)₂ n-Bu  85 S(O)₂ i-Bu  86 S(O)₂ allyl  87 S(O)₂ CH₂C≡CH  88 S(O)₂ CH═CH₂  89 S(O)₂ CH₂CH₂F  90 S(O)₂ CF₃  91 S(O)₂ CH₂CF₃  92 S(O)₂ CH₂CN  93 S(O)₂ cyclopropyl  94 S(O)₂ cyclopropylmethyl  95 S(O)₂ CH₂CO₂Me  96 S(O)₂ CH₂CH₂NMe₂  97 S(O)₂ CH₂-(N-morpholinyl)  98 S(O)₂ 2-chloropyridin-5-yl-methyl  99 S(O)₂ n-Hex 100 S(O)₂ 2-furanyl 101 S(O)₂ 2-pyrimidinyl 102 S(O)₂ 2-oxazolyl 103 S(O)₂ 5-[1,2,4]-oxadiazolyl 104 tetrazolyl 105 OC(O) H 106 OC(O) Me 107 OC(O) Et 108 OC(O) n-Pr 109 OC(O) i-Pr 110 OC(O) n-Bu 111 OC(O) i-Bu 112 OC(O) allyl 113 OC(O) CH₂C≡CH 114 OC(O) CH═CH₂ 115 OC(O) CH₂CH₂F 116 OC(O) CF₃ 117 OC(O) CH₂CF₃ 118 OC(O) CH₂CN 119 OC(O) cyclopropyl 120 OC(O) cyclopropylmethyl 121 OC(O) CH₂CO₂Me 122 OC(O) CH₂CH₂NMe₂ 123 OC(O) CH₂-(N-morpholinyl) 124 OC(O) 2-chloropyridin-5-yl-methyl 125 OC(O) n-Hex 126 OC(O) 2-furanyl 127 OC(O) 2-pyrimidinyl 128 OC(O) 2-oxazolyl 129 OC(O) 5-[1,2,4]-oxadiazolyl 130 OC(O) tetrazolyl 131 OC(O)O n-Hex 132 OC(O)O Me 133 OC(O)O Et 134 OC(O)O n-Pr 135 OC(O)O i-Pr 136 OC(O)O n-Bu 137 OC(O)O i-Bu 138 OC(O)O allyl 139 OC(O)O CH₂C≡CH 140 OC(O)O CH═CH₂ 141 OC(O)O CH₂CH₂F 142 OC(O)O CF₃ 143 OC(O)O CH₂CF₃ 144 OC(O)O CH₂CN 145 OC(O)O cyclopropyl 146 OC(O)O cyclopropylmethyl 147 OC(O)O CH₂CO₂Me 148 OC(O)O CH₂CH₂NMe₂ 149 OC(O)O CH₂-(N-morpholinyl) 150 OC(O)O 2-chloropyridin-5-yl-methyl 151 OC(O)O n-Hex 152 OC(O)O 2-furanyl 153 OC(O)O 2-pyrimidinyl 154 OC(O)O 2-oxazolyl 155 OC(O)O 5-[1,2,4]-oxadiazolyl 156 OC(O)O tetrazolyl 157 OC(O)NR′ H H 158 OC(O)NR′ Me H 159 OC(O)NR′ Et H 160 OC(O)NR′ n-Pr H 161 OC(O)NR′ i-Pr H 162 OC(O)NR′ n-Bu H 163 OC(O)NR′ i-Bu H 164 OC(O)NR′ allyl H 165 OC(O)NR′ CH₂C≡CH H 166 OC(O)NR′ CH═CH₂ H 167 OC(O)NR′ CH₂CH₂F H 168 OC(O)NR′ CF₃ H 169 OC(O)NR′ CH₂CF₃ H 170 OC(O)NR′ CH₂CN H 171 OC(O)NR′ cyclopropyl H 172 OC(O)NR′ cyclopropylmethyl H 173 OC(O)NR′ CH₂CO₂Me H 174 OC(O)NR′ CH₂CH₂NMe₂ H 175 OC(O)NR′ CH₂-(N-morpholinyl) H 176 OC(O)NR′ 2-chloropyridin-5-yl-methyl H 177 OC(O)NR′ n-Hex H 178 OC(O)NR′ 2-furanyl H 179 OC(O)NR′ 2-pyrimidinyl H 180 OC(O)NR′ 2-oxazolyl H 181 OC(O)NR′ 5-[1,2,4]-oxadiazolyl H 182 OC(O)NR′ tetrazolyl H 183 OC(O)NR′ H Me 184 OC(O)NR′ Me Me 185 OC(O)NR′ Et Me 186 OC(O)NR′ n-Pr Me 187 OC(O)NR′ i-Pr Me 188 OC(O)NR′ n-Bu Me 189 OC(O)NR′ i-Bu Me 190 OC(O)NR′ allyl Me 191 OC(O)NR′ CH₂C≡CH 192 OC(O)NR′ CH═CH₂ Me 193 OC(O)NR′ CH₂CH₂F Me 194 OC(O)NR′ CF₃ Me 195 OC(O)NR′ CH₂CF₃ Me 196 OC(O)NR′ CH₂CN Me 197 OC(O)NR′ cyclopropyl Me 198 OC(O)NR′ cyclopropylmethyl Me 199 OC(O)NR′ CH₂CO₂Me Me 200 OC(O)NR′ CH₂CH₂NMe₂ Me 201 OC(O)NR′ CH₂-(N-morpholinyl) Me 202 OC(O)NR′ 2-chloropyridin-5-yl-methyl Me 203 OC(O)NR′ n-Hex Me 204 OC(O)NR′ 2-furanyl Me 205 OC(O)NR′ 2-pyrimidinyl Me 206 OC(O)NR′ 2-oxazolyl Me 207 OC(O)NR′ 5-[1,2,4]-oxadiazolyl Me 208 OC(O)NR′ tetrazolyl Me 209 OC(O)NR′ H Et 210 OC(O)NR′ Me Et 211 OC(O)NR′ Et Et 212 OC(O)NR′ n-Pr Et 213 OC(O)NR′ i-Pr Et 214 OC(O)NR′ n-Bu Et 215 OC(O)NR′ i-Bu Et 216 OC(O)NR′ allyl Et 217 OC(O)NR′ CH₂C≡CH Et 218 OC(O)NR′ CH═CH₂ Et 219 OC(O)NR′ CH₂CH₂F Et 220 OC(O)NR′ CF₃ Et 221 OC(O)NR′ CH₂CF₃ Et 222 OC(O)NR′ CH₂CN Et 223 OC(O)NR′ cyclopropyl Et 224 OC(O)NR′ cyclopropylmethyl Et 225 OC(O)NR′ CH₂CO₂Me Et 226 OC(O)NR′ CH₂CH₂NMe₂ Et 227 OC(O)NR′ CH₂-(N-morpholinyl) Et 228 OC(O)NR′ 2-chloropyridin-5-yl-methyl Et 229 OC(O)NR′ 2-furanyl Et 230 OC(O)NR′ 2-pyrimidinyl Et 231 OC(O)NR′ 2-oxazolyl Et 232 OC(O)NR′ 5-[1,2,4]-oxadiazolyl Et 234 OC(O)NR′ tetrazolyl Et 235 OC(O)NR′ n-Hex Et 236 OC(O)C(O)O cyclobutyl 237 OC(O)C(O)O Me 238 OC(O)C(O)O Et 239 OC(O)C(O)O n-Pr 240 OC(O)C(O)O i-Pr 241 OC(O)C(O)O n-Bu 242 OC(O)C(O)O i-Bu 243 OC(O)C(O)O allyl 244 OC(O)C(O)O CH₂C≡CH 245 OC(O)C(O)O CH═CH₂ 246 OC(O)C(O)O CH₂CH₂F 247 OC(O)C(O)O CF₃ 248 OC(O)C(O)O CH₂CF₃ 249 OC(O)C(O)O CH₂CN 250 OC(O)C(O)O cyclopropyl 251 OC(O)C(O)O cyclopropylmethyl 252 OC(O)C(O)O CH₂CO₂Me 253 OC(O)C(O)O CH₂CH₂NMe₂ 254 OC(O)C(O)O CH₂-(N-morpholinyl) 255 OC(O)C(O)O 2-chloropyridin-5-yl-methyl 256 OC(O)C(O)O n-Hex 257 OC(O)C(O)O furanyl 258 OC(O)C(O)O 2-pyrimidinyl 259 OC(O)C(O)O 2-oxazolyl 260 OC(O)C(O)O 5-[1,2,4]-oxadiazolyl 261 OC(O)C(O)O tetrazolyl 262 S(O)₂NR′ H H 263 S(O)₂NR′ Me H 264 S(O)₂NR′ Et H 265 S(O)₂NR′ n-Pr H 266 S(O)₂NR′ i-Pr H 267 S(O)₂NR′ n-Bu H 268 S(O)₂NR′ i-Bu H 269 S(O)₂NR′ allyl H 270 S(O)₂NR′ CH₂C≡CH H 271 S(O)₂NR′ CH═CH₂ H 272 S(O)₂NR′ CH₂CH₂F H 273 S(O)₂NR′ CF₃ H 274 S(O)₂NR′ CH₂CF₃ H 275 S(O)₂NR′ CH₂CN H 276 S(O)₂NR′ cyclopropyl H 277 S(O)₂NR′ cyclopropylmethyl H 278 S(O)₂NR′ CH₂CO₂Me H 279 S(O)₂NR′ CH₂CH₂NMe₂ H 280 S(O)₂NR′ CH₂-(N-morpholinyl) H 281 S(O)₂NR′ 2-chloropyridin-5-yl-methyl H 282 S(O)₂NR′ n-Hex H 283 S(O)₂NR′ 2-furanyl H 284 S(O)₂NR′ 2-pyrimidinyl H 285 S(O)₂NR′ 2-oxazolyl H 286 S(O)₂NR′ 5-[1,2,4]-oxadiazolyl H 287 S(O)₂NR′ tetrazolyl H 288 S(O)₂NR′ H Me 289 S(O)₂NR′ Me Me 290 S(O)₂NR′ Et Me 300 S(O)₂NR′ n-Pr Me 301 S(O)₂NR′ i-Pr Me 302 S(O)₂NR′ n-Bu Me 303 S(O)₂NR′ i-Bu Me 304 S(O)₂NR′ allyl Me 305 S(O)₂NR′ CH₂C≡CH Me 306 S(O)₂NR′ CH═CH₂ Me 307 S(O)₂NR′ CH₂CH₂F Me 308 S(O)₂NR′ CF₃ Me 309 S(O)₂NR′ CH₂CF₃ Me 310 S(O)₂NR′ CH₂CN Me 311 S(O)₂NR′ cyclopropyl Me 312 S(O)₂NR′ cyclopropylmethyl Me 313 S(O)₂NR′ CH₂CO₂Me Me 314 S(O)₂NR′ CH₂CH₂NMe₂ Me 315 S(O)₂NR′ CH₂-(N-morpholinyl) Me 316 S(O)₂NR′ 2-chloropyridin-5-yl-methyl Me 317 S(O)₂NR′ n-Hex Me 318 S(O)₂NR′ 2-furanyl Me 319 S(O)₂NR′ 2-pyrimidinyl Me 320 S(O)₂NR′ 2-oxazolyl Me 321 S(O)₂NR′ 5-[1,2,4]-oxadiazolyl Me 322 S(O)₂NR′ tetrazolyl Me 323 S(O)₂NR′ H Et 324 S(O)₂NR′ Me Et 325 S(O)₂NR′ Et Et 326 S(O)₂NR′ n-Pr Et 327 S(O)₂NR′ i-Pr Et 328 S(O)₂NR′ n-Bu Et 329 S(O)₂NR′ i-Bu Et 330 S(O)₂NR′ allyl Et 331 S(O)₂NR′ CH₂C≡CH Et 332 S(O)₂NR′ CH═CH₂ Et 333 S(O)₂NR′ CH₂CH₂F Et 334 S(O)₂NR′ CF₃ Et 335 S(O)₂NR′ CH₂CF₃ Et 336 S(O)₂NR′ CH₂CN Et 337 S(O)₂NR′ cyclopropyl Et 338 S(O)₂NR′ cyclopropylmethyl Et 339 S(O)₂NR′ CH₂CO₂Me Et 340 S(O)₂NR′ CH₂CH₂NMe₂ Et 341 S(O)₂NR′ CH₂-(N-morpholinyl) Et 342 S(O)₂NR′ 2-chloropyridin-5-yl-methyl Et 344 S(O)₂NR′ n-Hex Et 345 S(O)₂NR′ 2-furanyl Et 346 S(O)₂NR′ 2-pyrimidinyl Et 347 S(O)₂NR′ 2-oxazolyl Et 348 S(O)₂NR′ 5-[1,2,4]-oxadiazolyl Et 349 S(O)₂NR′ tetrazolyl Et

TABLE 5

Ex. m.p. No. Y R R′ [° C.]  1 O H  2 O Me  3 O Et  4 O n-Pr  5 O i-Pr  6 O n-Bu  7 O i-Bu  8 O allyl  9 O CH₂C≡CH  10 O CH═CH₂  11 O CH₂CH₂F  12 O CF₃  13 O CH₂CF₃  14 O CH₂CN  15 O cyclopropyl  16 O cyclopropylmethyl  17 O CH₂CO₂Me  18 O CH₂CH₂NMe₂  19 O CH₂-(N-morpholinyl)  20 O 2-chloropyridin-5-yl-methyl  21 O n-Hex  22 O 2-furanyl  23 O 2-pyrimidinyl  24 O 2-oxazolyl  25 O 5-[1,2,4]-oxadiazolyl  26 O tetrazolyl  27 S H  28 S Me  29 S Et  30 S n-Pr  31 S i-Pr  32 S n-Bu  33 S i-Bu  33 S allyl  34 S CH₂C≡CH  35 S tetrazolyl  36 S CH═CH₂  37 S CH₂CH₂F  38 S CF₃  39 S CH₂CF₃  40 S CH₂CN  41 S cyclopropyl  42 S cyclopropylmethyl  43 S CH₂CO₂Me  44 S CH₂CH₂NMe₂  45 S CH₂-(N-morpholinyl)  46 S 2-chloropyridin-5-yl-methyl  47 S n-Hex  48 S 2-furanyl  49 S 2-pyrimidinyl  50 S 2-oxazolyl  51 S 5-[1,2,4]-oxadiazolyl  51a S tetrazolyl  52 S(O) cyclobutyl  53 S(O) Me  54 S(O) Et  55 S(O) n-Pr  56 S(O) i-Pr  57 S(O) n-Bu  58 S(O) i-Bu  59 S(O) allyl  60 S(O) CH₂C≡CH  61 S(O) CH═CH₂  62 S(O) CH₂CH₂F  63 S(O) CF₃  64 S(O) CH₂CF₃  65 S(O) CH₂CN  66 S(O) cyclopropyl  67 S(O) cyclopropylmethyl  68 S(O) CH₂CO₂Me  69 S(O) CH₂CH₂NMe₂  70 S(O) CH₂-(N-morpholinyl)  71 S(O) 2-chloropyridin-5-yl-methyl  72 S(O) n-Hex  73 S(O) 2-furanyl  74 S(O) 2-pyrimidinyl  75 S(O) 2-oxazolyl  76 S(O) 5-[1,2,4]-oxadiazolyl  77 S(O) tetrazolyl  78 S(O)₂ cyclobutyl  79 S(O)₂ Me  80 S(O)₂ Et  81 S(O)₂ n-Pr  82 S(O)₂ i-Pr  83 S(O)₂ n-Bu  84 S(O)₂ i-Bu  85 S(O)₂ allyl  86 S(O)₂ CH₂C≡CH  87 S(O)₂ CH═CH₂  88 S(O)₂ CH₂CH₂F  89 S(O)₂ CF₃  90 S(O)₂ CH₂CF₃  91 S(O)₂ CH₂CN  92 S(O)₂ cyclopropyl  93 S(O)₂ cyclopropylmethyl  94 S(O)₂ CH₂CO₂Me  95 S(O)₂ CH₂CH₂NMe₂  96 S(O)₂ CH₂-(N-morpholinyl)  97 S(O)₂ 2-chloropyridin-5-yl-methyl  98 S(O)₂ n-Hex  99 S(O)₂ 2-furanyl 100 S(O)₂ 2-pyrimidinyl 101 S(O)₂ 2-oxazolyl 102 S(O)₂ 5-[1,2,4]-oxadiazolyl 103 S(O)₂ tetrazolyl 104 OC(O) H 105 OC(O) Me 106 OC(O) Et 107 OC(O) n-Pr 108 OC(O) i-Pr 109 OC(O) n-Bu 110 OC(O) i-Bu 111 OC(O) allyl 112 OC(O) CH₂C≡CH 113 OC(O) CH═CH₂ 114 OC(O) CH₂CH₂F 115 OC(O) CF₃ 116 OC(O) CH₂CF₃ 117 OC(O) CH₂CN 118 OC(O) cyclopropyl 119 OC(O) cyclopropylmethyl 120 OC(O) CH₂CO₂Me 121 OC(O) CH₂CH₂NMe₂ 122 OC(O) CH₂-(N-morpholinyl) 123 OC(O) 2-chloropyridin-5-yl-methyl 124 OC(O) n-Hex 125 OC(O) 2-furanyl 126 OC(O) 2-pyrimidinyl 127 OC(O) 2-oxazolyl 128 OC(O) 5-[1,2,4]-oxadiazolyl 129 OC(O) tetrazolyl 130 OC(O)O cyclobutyl 131 OC(O)O Me 132 OC(O)O Et 133 OC(O)O n-Pr 134 OC(O)O i-Pr 135 OC(O)O n-Bu 136 OC(O)O i-Bu 137 OC(O)O allyl 138 OC(O)O CH₂C≡CH 139 OC(O)O CH═CH₂ 140 OC(O)O CH₂CH₂F 141 OC(O)O CF₃ 142 OC(O)O CH₂CF₃ 143 OC(O)O CH₂CN 144 OC(O)O cyclopropyl 145 OC(O)O cyclopropylmethyl 146 OC(O)O CH₂CO₂Me 147 OC(O)O CH₂CH₂NMe₂ 148 OC(O)O CH₂-(N-morpholinyl) 149 OC(O)O 2-chloropyridin-5-yl-methyl 150 OC(O)O n-Hex 151 OC(O)O 2-furanyl 152 OC(O)O 2-pyrimidinyl 153 OC(O)O 2-oxazolyl 154 OC(O)O 5-[1,2,4]-oxadiazolyl 155 OC(O)O tetrazolyl 156 OC(O)NR′ H H 157 OC(O)NR′ Me H 158 OC(O)NR′ Et H 159 OC(O)NR′ n-Pr H 160 OC(O)NR′ i-Pr H 161 OC(O)NR′ n-Bu H 162 OC(O)NR′ i-Bu H 163 OC(O)NR′ allyl H 164 OC(O)NR′ CH₂C≡CH H 165 OC(O)NR′ CH═CH₂ H 166 OC(O)NR′ CH₂CH₂F H 167 OC(O)NR′ CF₃ H 168 OC(O)NR′ CH₂CF₃ H 169 OC(O)NR′ CH₂CN H 170 OC(O)NR′ cyclopropyl H 171 OC(O)NR′ cyclopropylmethyl H 172 OC(O)NR′ CH₂CO₂Me H 173 OC(O)NR′ CH₂CH₂NMe₂ H 174 OC(O)NR′ CH₂-(N-morpholinyl) H 175 OC(O)NR′ 2-chloropyridin-5-yl-methyl H 176 OC(O)NR′ n-Hex H 177 OC(O)NR′ 2-furanyl H 178 OC(O)NR′ 2-pyrimidinyl H 179 OC(O)NR′ 2-oxazolyl H 180 OC(O)NR′ 5-[1,2,4]-oxadiazolyl H 181 OC(O)NR′ tetrazolyl H 182 OC(O)NR′ H Me 183 OC(O)NR′ Me Me 184 OC(O)NR′ Et Me 185 OC(O)NR′ n-Pr Me 186 OC(O)NR′ i-Pr Me 187 OC(O)NR′ n-Bu Me 188 OC(O)NR′ i-Bu Me 189 OC(O)NR′ allyl Me 190 OC(O)NR′ CH₂C≡CH Me 200 OC(O)NR′ CH═CH₂ Me 201 OC(O)NR′ CH₂CH₂F Me 202 OC(O)NR′ CF₃ Me 203 OC(O)NR′ CH₂CF₃ Me 204 OC(O)NR′ CH₂CN Me 205 OC(O)NR′ cyclopropyl Me 206 OC(O)NR′ cyclopropylmethyl Me 207 OC(O)NR′ CH₂CO₂Me Me 208 OC(O)NR′ CH₂CH₂NMe₂ Me 209 OC(O)NR′ CH₂-(N-morpholinyl) Me 210 OC(O)NR′ 2-chloropyridin-5-yl-methyl Me 211 OC(O)NR′ n-Hex Me 212 OC(O)NR′ 2-furanyl Me 213 OC(O)NR′ 2-pyrimidinyl Me 214 OC(O)NR′ 2-oxazolyl Me 215 OC(O)NR′ 5-[1,2,4]-oxadiazolyl Me 216 OC(O)NR′ tetrazolyl Me 217 OC(O)NR′ H Et 218 OC(O)NR′ Me Et 219 OC(O)NR′ Et Et 220 OC(O)NR′ n-Pr Et 221 OC(O)NR′ i-Pr Et 222 OC(O)NR′ n-Bu Et 223 OC(O)NR′ i-Bu Et 224 OC(O)NR′ allyl Et 225 OC(O)NR′ CH₂C≡CH Et 226 OC(O)NR′ CH═CH₂ Et 227 OC(O)NR′ CH₂CH₂F Et 228 OC(O)NR′ CF₃ Et 229 OC(O)NR′ CH₂CF₃ Et 230 OC(O)NR′ CH₂CN Et 231 OC(O)NR′ cyclopropyl Et 232 OC(O)NR′ cyclopropylmethyl Et 233 OC(O)NR′ CH₂CO₂Me Et 234 OC(O)NR′ CH₂CH₂NMe₂ Et 235 OC(O)NR′ CH₂-(N-morpholinyl) Et 236 OC(O)NR′ 2-chloropyridin-5-yl-methyl Et 237 OC(O)NR′ n-Hex Et 238 OC(O)NR′ 2-furanyl Et 239 OC(O)NR′ 2-pyrimidinyl Et 240 OC(O)NR′ 2-oxazolyl Et 241 OC(O)NR′ 5-[1,2,4]-oxadiazolyl Et 242 OC(O)NR′ tetrazolyl Et 243 OC(O)C(O)O cyclobutyl 244 OC(O)C(O)O Me 245 OC(O)C(O)O Et 246 OC(O)C(O)O n-Pr 247 OC(O)C(O)O i-Pr 248 OC(O)C(O)O n-Bu 249 OC(O)C(O)O i-Bu 250 OC(O)C(O)O allyl 251 OC(O)C(O)O CH₂C≡CH 252 OC(O)C(O)O CH═CH₂ 253 OC(O)C(O)O CH₂CH₂F 254 OC(O)C(O)O CF₃ 255 OC(O)C(O)O CH₂CF₃ 256 OC(O)C(O)O CH₂CN 257 OC(O)C(O)O cyclopropyl 258 OC(O)C(O)O cyclopropylmethyl 259 OC(O)C(O)O CH₂CO₂Me 260 OC(O)C(O)O CH₂CH₂NMe₂ 261 OC(O)C(O)O CH₂-(N-morpholinyl) 262 OC(O)C(O)O 2-chloropyridin-5-yl-methyl 263 OC(O)C(O)O n-Hex 264 OC(O)C(O)O 2-furanyl 265 OC(O)C(O)O 2-pyrimidinyl 266 OC(O)C(O)O 2-oxazolyl 267 OC(O)C(O)O 5-[1,2,4]-oxadiazolyl 268 OC(O)C(O)O tetrazolyl 269 S(O)₂NR′ H Me 270 S(O)₂NR′ Me Me 271 S(O)₂NR′ Et Me 272 S(O)₂NR′ n-Pr Me 273 S(O)₂NR′ i-Pr Me 274 S(O)₂NR′ n-Bu Me 275 S(O)₂NR′ i-Bu Me 276 S(O)₂NR′ allyl Me 277 S(O)₂NR′ CH₂C≡CH Me 278 S(O)₂NR′ CH═CH₂ Me 279 S(O)₂NR′ CH₂CH₂F Me 280 S(O)₂NR′ CF₃ Me 281 S(O)₂NR′ CH₂CF₃ Me 282 S(O)₂NR′ CH₂CN Me 283 S(O)₂NR′ cyclopropyl Me 284 S(O)₂NR′ cyclopropylmethyl Me 285 S(O)₂NR′ CH₂CO₂Me Me 286 S(O)₂NR′ CH₂CH₂NMe₂ Me 287 S(O)₂NR′ CH₂-(N-morpholinyl) Me 288 S(O)₂NR′ 2-chloropyridin-5-yl-methyl Me 289 S(O)₂NR′ n-Hex Me 290 S(O)₂NR′ 2-furanyl Me 291 S(O)₂NR′ 2-pyrimidinyl Me 292 S(O)₂NR′ 2-oxazolyl Me 293 S(O)₂NR′ 5-[1,2,4]-oxadiazolyl Me 294 S(O)₂NR′ tetrazolyl Me 295 S(O)₂NR′ H Et 296 S(O)₂NR′ Me Et 297 S(O)₂NR′ Et Et 298 S(O)₂NR′ n-Pr Et 299 S(O)₂NR′ i-Pr Et 300 S(O)₂NR′ n-Bu Et 301 S(O)₂NR′ i-Bu Et 302 S(O)₂NR′ allyl Et 303 S(O)₂NR′ CH₂C≡CH Et 304 S(O)₂NR′ CH═CH₂ Et 305 S(O)₂NR′ CH₂CH₂F Et 306 S(O)₂NR′ CF₃ Et 307 S(O)₂NR′ CH₂CF₃ Et 308 S(O)₂NR′ CH₂CN Et 309 S(O)₂NR′ cyclopropyl Et 310 S(O)₂NR′ cyclopropylmethyl Et 311 S(O)₂NR′ CH₂CO₂Me Et 312 S(O)₂NR′ CH₂CH₂NMe₂ Et 313 S(O)₂NR′ CH₂-(N-morpholinyl) Et 314 S(O)₂NR′ 2-chloropyridin-5-yl-methyl Et 315 S(O)₂NR′ n-Hex Et 316 S(O)₂NR′ 2-furanyl Et 317 S(O)₂NR′ 2-pyrimidinyl Et 318 S(O)₂NR′ 2-oxazolyl Et 319 S(O)₂NR′ 5-[1,2,4]-oxadiazolyl Et 320 S(O)₂NR′ tetrazolyl Et

TABLE 6

m.p. Ex. No. Y R R′ [° C.]  1 O H  2 O Me  3 O Et  4 O n-Pr  5 O i-Pr  6 O n-Bu  7 O i-Bu  8 O allyl  9 O CH₂C≡CH  10 O CH═CH₂  11 O CH₂CH₂F  12 O CF₃  13 O CH₂CF₃  14 O CH₂CN  15 O cyclopropyl  16 O cyclopropylmethyl  17 O CH₂CO₂Me  18 O CH₂CH₂NMe₂  19 O CH₂—(N-morpholinyl)  20 O 2-chloropyridin-5-yl-methyl  21 O 2-furanyl  22 O 2-pyrimidinyl  23 O 2-oxazolyl  24 O 5-[1,2,4]-oxadiazolyl  25 O tetrazolyl  26 S H  27 S Me  28 S Et  29 S n-Pr  30 S i-Pr  31 S n-Bu  32 S i-Bu  33 S allyl  34 S CH₂C≡CH  35 S CH═CH₂  36 S CH₂CH₂F  37 S CF₃  38 S CH₂CF₃  39 S CH₂CN  40 S cyclopropyl  41 S cyclopropylmethyl  42 S CH₂CO₂Me  43 S CH₂CH₂NMe₂  44 S CH₂—(N-morpholinyl)  45 S 2-chloropyridin-5-yl-methyl  46 S 2-furanyl  47 S 2-pyrimidinyl  48 S 2-oxazolyl  49 S 5-[1,2,4]-oxadiazolyl  50 S tetrazolyl  51 S(O) n-Hex  52 S(O) Me  53 S(O) Et  54 S(O) n-Pr  55 S(O) i-Pr  56 S(O) n-Bu  57 S(O) i-Bu  58 S(O) allyl  59 S(O) CH₂C≡CH  60 S(O) CH═CH₂  61 S(O) CH₂CH₂F  62 S(O) CF₃  63 S(O) CH₂CF₃  64 S(O) CH₂CN  65 S(O) cyclopropyl  66 S(O) cyclopropylmethyl  67 S(O) CH₂CO₂Me  68 S(O) CH₂CH₂NMe₂  69 S(O) CH₂—(N-morpholinyl)  70 S(O) 2-chloropyridin-5-yl-methyl  71 S(O) 2-furanyl  72 S(O) 2-pyrimidinyl  73 S(O) 2-oxazolyl  74 S(O) 5-[1,2,4]-oxadiazolyl  75 S(O) tetrazolyl  76 S(O)₂ n-Hex  77 S(O)₂ Me  78 S(O)₂ Et  79 S(O)₂ n-Pr  80 S(O)₂ i-Pr  81 S(O)₂ n-Bu  82 S(O)₂ i-Bu  83 S(O)₂ allyl  84 S(O)₂ CH₂C≡CH  85 S(O)₂ CH═CH₂  86 S(O)₂ CH₂CH₂F  87 S(O)₂ CF₃  88 S(O)₂ CH₂CF₃  89 S(O)₂ CH₂CN  90 S(O)₂ cyclopropyl  91 S(O)₂ cyclopropylmethyl  92 S(O)₂ CH₂CO₂Me  93 S(O)₂ CH₂CH₂NMe₂  94 S(O)₂ CH₂—(N-morpholinyl)  95 S(O)₂ 2-chloropyridin-5-yl-methyl  96 S(O)₂ 2-furanyl  97 S(O)₂ 2-pyrimidinyl  98 S(O)₂ 2-oxazolyl  99 S(O)₂ 5-[1,2,4]-oxadiazolyl 100 S(O)₂ tetrazolyl 101 OC(O) H 102 OC(O) Me 103 OC(O) Et 104 OC(O) n-Pr 105 OC(O) i-Pr 106 OC(O) n-Bu 107 OC(O) i-Bu 108 OC(O) allyl 109 OC(O) CH₂C≡CH 110 OC(O) CH═CH₂ 111 OC(O) CH₂CH₂F 112 OC(O) CF₃ 113 OC(O) CH₂CF₃ 114 OC(O) CH₂CN 115 OC(O) cyclopropyl 116 OC(O) cyclopropylmethyl 117 OC(O) CH₂CO₂Me 118 OC(O) CH₂CH₂NMe₂ 119 OC(O) CH₂—(N-morpholinyl) 120 OC(O) 2-chloropyridin-5-yl-methyl 121 OC(O) 2-furanyl 122 OC(O) 2-pyrimidinyl 123 OC(O) 2-oxazolyl 124 OC(O) 5-[1,2,4]-oxadiazolyl 125 OC(O) tetrazolyl 126 OC(O)O n-Hex 127 OC(O)O Me 128 OC(O)O Et 129 OC(O)O n-Pr 130 OC(O)O i-Pr 131 OC(O)O n-Bu 132 OC(O)O i-Bu 133 OC(O)O allyl 134 OC(O)O CH₂C≡CH 135 OC(O)O CH═CH₂ 136 OC(O)O CH₂CH₂F 137 OC(O)O CF₃ 138 OC(O)O CH₂CF₃ 139 OC(O)O CH₂CN 140 OC(O)O cyclopropyl 141 OC(O)O cyclopropylmethyl 142 OC(O)O CH₂CO₂Me 143 OC(O)O CH₂CH₂NMe₂ 144 OC(O)O CH₂—(N-morpholinyl) 145 OC(O)O 2-chloropyridin-5-yl-methyl 146 OC(O)O 2-furanyl 147 OC(O)O 2-pyrimidinyl 148 OC(O)O 2-oxazolyl 149 OC(O)O 5-[1,2,4]-oxadiazolyl 150 OC(O)O tetrazolyl 151 OC(O)NR′ H H 152 OC(O)NR′ Me H 153 OC(O)NR′ Et H 154 OC(O)NR′ n-Pr H 155 OC(O)NR′ i-Pr H 156 OC(O)NR′ n-Bu H 157 OC(O)NR′ i-Bu H 158 OC(O)NR′ allyl H 159 OC(O)NR′ CH₂C≡CH H 160 OC(O)NR′ CH═CH₂ H 161 OC(O)NR′ CH₂CH₂F H 162 OC(O)NR′ CF₃ H 163 OC(O)NR′ CH₂CF₃ H 164 OC(O)NR′ CH₂CN H 165 OC(O)NR′ cyclopropyl H 166 OC(O)NR′ cyclopropylmethyl H 167 OC(O)NR′ CH₂CO₂Me H 168 OC(O)NR′ CH₂CH₂NMe₂ H 169 OC(O)NR′ CH₂—(N-morpholinyl) H 170 OC(O)NR′ 2-chloropyridin-5-yl-methyl H 171 OC(O)NR′ 2-furanyl H 172 OC(O)NR′ 2-pyrimidinyl H 173 OC(O)NR′ 2-oxazolyl H 174 OC(O)NR′ 5-[1,2,4]-oxadiazolyl H 175 OC(O)NR′ tetrazolyl H 176 OC(O)NR′ H Me 177 OC(O)NR′ Me Me 178 OC(O)NR′ Et Me 179 OC(O)NR′ n-Pr Me 180 OC(O)NR′ i-Pr Me 181 OC(O)NR′ n-Bu Me 182 OC(O)NR′ i-Bu Me 183 OC(O)NR′ allyl Me 184 OC(O)NR′ CH₂C≡CH Me 185 OC(O)NR′ CH═CH₂ Me 186 OC(O)NR′ CH₂CH₂F Me 187 OC(O)NR′ CF₃ Me 188 OC(O)NR′ CH₂CF₃ Me 189 OC(O)NR′ CH₂CN Me 190 OC(O)NR′ cyclopropyl Me 191 OC(O)NR′ cyclopropylmethyl Me 192 OC(O)NR′ CH₂CO₂Me Me 193 OC(O)NR′ CH₂CH₂NMe₂ Me 194 OC(O)NR′ CH₂—(N-morpholinyl) Me 195 OC(O)NR′ 2-chloropyridin-5-yl-methyl Me 196 OC(O)NR′ furanyl Me 197 OC(O)NR′ 2-pyrimidinyl Me 198 OC(O)NR′ 2-oxazolyl Me 199 OC(O)NR′ 5-[1,2,4]-oxadiazolyl Me 200 OC(O)NR′ tetrazolyl Me 201 OC(O)NR′ H Et 202 OC(O)NR′ Me Et 203 OC(O)NR′ Et Et 204 OC(O)NR′ n-Pr Et 205 OC(O)NR′ i-Pr Et 206 OC(O)NR′ n-Bu Et 207 OC(O)NR′ i-Bu Et 208 OC(O)NR′ allyl Et 209 OC(O)NR′ CH₂C≡CH Et 210 OC(O)NR′ CH═CH₂ Et 211 OC(O)NR′ CH₂CH₂F Et 212 OC(O)NR′ CF₃ Et 213 OC(O)NR′ CH₂CF₃ Et 214 OC(O)NR′ CH₂CN Et 215 OC(O)NR′ cyclopropyl Et 216 OC(O)NR′ cyclopropylmethyl Et 217 OC(O)NR′ CH₂CO₂Me Et 218 OC(O)NR′ CH₂CH₂NMe₂ Et 219 OC(O)NR′ CH₂—(N-morpholinyl) Et 220 OC(O)NR′ 2-chloropyridin-5-yl-methyl Et 221 OC(O)NR′ 2-furanyl Et 222 OC(O)NR′ 2-pyrimidinyl Et 223 OC(O)NR′ 2-oxazolyl Et 224 OC(O)NR′ 5-[1,2,4]-oxadiazolyl Et 225 OC(O)NR′ tetrazolyl Et 226 OC(O)C(O)O n-Hex 227 OC(O)C(O)O Me 228 OC(O)C(O)O Et 229 OC(O)C(O)O n-Pr 230 OC(O)C(O)O i-Pr 231 OC(O)C(O)O n-Bu 232 OC(O)C(O)O i-Bu 233 OC(O)C(O)O allyl 234 OC(O)C(O)O CH₂C≡CH 235 OC(O)C(O)O CH═CH₂ 236 OC(O)C(O)O CH₂CH₂F 237 OC(O)C(O)O CF₃ 238 OC(O)C(O)O CH₂CF₃ 239 OC(O)C(O)O CH₂CN 240 OC(O)C(O)O cyclopropyl 241 OC(O)C(O)O cyclopropylmethyl 242 OC(O)C(O)O CH₂CO₂Me 243 OC(O)C(O)O CH₂CH₂NMe₂ 244 OC(O)C(O)O CH₂—(N-morpholinyl) 245 OC(O)C(O)O 2-chloropyridin-5-yl-methyl 246 OC(O)C(O)O 2-furanyl 247 OC(O)C(O)O 2-pyrimidinyl 248 OC(O)C(O)O 2-oxazolyl 249 OC(O)C(O)O 5-[1,2,4]-oxadiazolyl 250 OC(O)C(O)O tetrazolyl 251 S(O)₂NR′ H H 252 S(O)₂NR′ Me H 253 S(O)₂NR′ Et H 254 S(O)₂NR′ n-Pr H 255 S(O)₂NR′ i-Pr H 256 S(O)₂NR′ n-Bu H 257 S(O)₂NR′ i-Bu H 258 S(O)₂NR′ allyl H 259 S(O)₂NR′ CH₂C≡CH H 260 S(O)₂NR′ CH═CH₂ H 261 S(O)₂NR′ CH₂CH₂F H 262 S(O)₂NR′ CF₃ H 263 S(O)₂NR′ CH₂CF₃ H 264 S(O)₂NR′ CH₂CN H 265 S(O)₂NR′ cyclopropyl H 266 S(O)₂NR′ cyclopropylmethyl H 267 S(O)₂NR′ CH₂CO₂Me H 268 S(O)₂NR′ CH₂CH₂NMe₂ H 269 S(O)₂NR′ CH₂—(N-morpholinyl) H 270 S(O)₂NR′ 2-chloropyridin-5-yl-methyl H 271 S(O)₂NR′ 2-furanyl H 272 S(O)₂NR′ 2-pyrimidinyl H 273 S(O)₂NR′ 2-oxazolyl H 274 S(O)₂NR′ 5-[1,2,4]-oxadiazolyl H 275 S(O)₂NR′ tetrazolyl H 276 S(O)₂NR′ H Me 277 S(O)₂NR′ Me Me 278 S(O)₂NR′ Et Me 279 S(O)₂NR′ n-Pr Me 280 S(O)₂NR′ i-Pr Me 281 S(O)₂NR′ n-Bu Me 282 S(O)₂NR′ i-Bu Me 283 S(O)₂NR′ allyl Me 284 S(O)₂NR′ CH₂C≡CH Me 285 S(O)₂NR′ CH═CH₂ Me 286 S(O)₂NR′ CH₂CH₂F Me 287 S(O)₂NR′ CF₃ Me 288 S(O)₂NR′ CH₂CF₃ Me 289 S(O)₂NR′ CH₂CN Me 290 S(O)₂NR′ cyclopropyl Me 291 S(O)₂NR′ cyclopropylmethyl Me 292 S(O)₂NR′ CH₂CO₂Me Me 293 S(O)₂NR′ CH₂CH₂NMe₂ Me 294 S(O)₂NR′ CH₂—(N-morpholinyl) Me 295 S(O)₂NR′ 2-chloropyridin-5-yl-methyl Me 296 S(O)₂NR′ 2-furanyl Me 297 S(O)₂NR′ 2-pyrimidinyl Me 298 S(O)₂NR′ 2-oxazolyl Me 299 S(O)₂NR′ 5-[1,2,4]-oxadiazolyl Me 300 S(O)₂NR′ tetrazolyl Me 301 S(O)₂NR′ H Et 302 S(O)₂NR′ Me Et 303 S(O)₂NR′ Et Et 304 S(O)₂NR′ n-Pr Et 305 S(O)₂NR′ i-Pr Et 306 S(O)₂NR′ n-Bu Et 307 S(O)₂NR′ i-Bu Et 308 S(O)₂NR′ allyl Et 309 S(O)₂NR′ CH₂C≡CH Et 310 S(O)₂NR′ CH═CH₂ Et 311 S(O)₂NR′ CH₂CH₂F Et 312 S(O)₂NR′ CF₃ Et 313 S(O)₂NR′ CH₂CF₃ Et 314 S(O)₂NR′ CH₂CN Et 315 S(O)₂NR′ cyclopropyl Et 316 S(O)₂NR′ cyclopropylmethyl Et 317 S(O)₂NR′ CH₂CO₂Me Et 318 S(O)₂NR′ CH₂CH₂NMe₂ Et 319 S(O)₂NR′ CH₂—(N-morpholinyl) Et 320 S(O)₂NR′ 2-chloropyridin-5-yl-methyl Et 321 S(O)₂NR′ 2-furanyl Et 322 S(O)₂NR′ 2-pyrimidinyl Et 323 S(O)₂NR′ 2-oxazolyl Et 324 S(O)₂NR′ 5-[1,2,4]-oxadiazolyl Et 325 S(O)₂NR′ tetrazolyl Et

B. Formulation Examples

a) A dusting powder is obtained by mixing 10 parts by weight of active compound and 90 parts by weight of talc, as inert substance, and comminuting the mixture in an impact mill.

b) A wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of active compound, 65 parts by weight of kaolin-containing quartz, as the inert substance, 10 parts by weight of potassium ligninsulfonate and 1 part by weight of sodium oleoylmethyltaurinate, as wetting and dispersing agent, and grinding the mixture in a pinned disk mill.

c) A dispersion concentrate which is readily dispersible in water is prepared by mixing 40 parts by weight of active compound with 7 parts by weight of a sulfosuccinic monoester, 2 parts by weight of a sodium ligninsulfonate and 51 parts by weight of water and grinding the mixture to a fineness of below 5 microns in a grinding bead mill.

d) An emulsifiable concentrate can be prepared from 15 parts by weight of active compound, 75 parts by weight of cyclohexane, as the solvent, and 10 parts by weight of ethoxylated nonylphenol (10 EO), as the emulsifier.

e) Granules can be prepared from 2 to 15 parts by weight of active compound and an inert granule carrier material, such as attapulgite, pumice granules and/or quartz sand. A suspension of the wettable powder from Example b) having a solids content of 30% is expediently used, and this is sprayed onto the surface of attapulgite granules and the components are dried and mixed intimately. The weight content of the wettable powder is approximately 5% and that of the inert carrier material is approximately 95% of the finished granules.

C. Biological Examples

Example 1

Germinated broad bean seeds (Vicia faba) with radicles were transferred into brown glass bottles filled with tap water and subsequently populated with approximately 100 black bean aphids (Aphis fabae). Plants and aphids were then dipped for 5 seconds into an aqueous solution of the formulated preparation to be examined. After the solution had dripped off, plants and animals were kept in a climatized chamber (16 hours of light/day, 25° C., 40-60% relative atmospheric humidity). After 3 and 6 days storage, the effect of the preparation on the aphids was determined. At a concentration of 300 ppm (based on the content of active compound), the preparations of Example Nos. 2/29, 2/43, 2/67, 2/6, 3/6, 3/50, 3/75 and 3/49 effected a mortality of 90-100% among the aphids.

The compounds are numbered with the Table/No. in the table.

Example 2

The leaves of 12 rice plants having a stem length of 8 cm were dipped for 5 seconds into an aqueous solution of the formulated preparation to be examined. After the solution had dripped off, the rice plants treated in this manner were placed in a Petri dish and populated with approximately 20 larvae (L3 stage) of the rice leafhopper species Nilaparvata lugens. The Petri dish was closed and stored in a climatized chamber (16 hours of light/day, 25° C., 40-60% relative atmospheric humidity). After 6 days storage, the mortality among the leafhopper larvae was determined. At a concentration of 300 ppm (based on the content of active compound), the preparations of Example Nos. 2/97, 2/127, 2/153, 2/255, 3/50 and 3/75 effected a mortality of 90-100%.

Example 3

Germinated broad bean seeds (Vicia faba) with radicles were transferred into brown glass bottles filled with tap water. Four milliliters of an aqueous solution of the formulated preparation to be examined were pipetted into the brown glass bottle. The broad bean was subsequently heavily populated with approximately 100 black bean aphids (Aphis fabae). Plants and animals were then stored in a climatized chamber (16 hours of light/day, 25° C., 40-60% relative atmospheric humidity). After 3 and 6 days storage, the root-systemic activity of the preparation on the aphids was determined. At a concentration of 30 ppm (based on the content of active compound), the preparations of Example Nos. 2/29, 2/43, 2/55, 2/67, 2/97, 2/6, 2/167, 2/153, 3/6, 3/50, 3/75 and 3/49 effected a mortality of 90-100% among the aphids by root-systemic action.

Although preferred embodiments of the present invention and modifications thereof have been described in detail herein, it is to be understood that this invention is not limited to those precise embodiments and modifications, and that other modifications and variations may be affected by one skilled in the art without departing from the spirit and scope of the invention as defined by the appended claims. 

What is claimed is:
 1. A 4-trifluoromethyl-3-oxadiazolylpyridine of the formula (I′), or a salt thereof,

wherein m is 0 or 1; X′ is a single bond, a straight-chain alkylene group having 1, 2 or 3 carbon atoms or a branched alkylene group having 3 to 9 carbon atoms, where one or more H atoms may be replaced by F; Y′ is —O—, —S—, —SO₂—, —O—CO—, —O—CO—O—, —SO₂—O—, —O—SO₂—, —NR¹—, —NR²—CO—, —NR³—CO—O—, —NR⁴—CO—NR⁵—, —O—CO—CO—O—, —O—CO—NR⁶—, —SO₂—NR⁷— or —NR⁸—SO₂—; R,R¹,R²,R³,R⁴,R⁵,R⁶,R⁷,R⁸ are identical or different and are independently of one another H, (C₁-C₁₀)-alkyl, (C₂-C₁₀)-alkenyl, (C₂-Cl₁₀)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl, (C₆-C₈)-cycloalkynyl, heterocyclyl or —(CH₂)₁₋₄-heterocyclyl, where each of the eight last-mentioned groups is unsubstituted or mono- or polysubstituted, and where, optionally R and R¹, R and R², R and R⁵, R and R⁶, R and R⁷, R and R⁸ or X′ and R, together form a ring system, with the proviso, that the compounds in which X′=-, Y′=O, R=H X′=-, Y′=O, R=Me X′=-, Y′=O, R=Et X′=-, Y′=O, R=CHF₂ X′=-, Y′=O, R=CH₂Ph X′=CH₂, Y′=O, R=2-furanyl X′=CH₂, Y′=O, R=Me X′=CH₂, Y′=O, R=5-isoxazolyl X′=CH₂, Y′=O, R=5-nitrofuran-2-yl X′=CH₂CH₂, Y′=O, R=H X′=CH₂CH₂; Y′=O, R=Me X′=CH₂CH₂, Y′=O,

X′=CH₂CH₂, Y′=O, R=Et X′=CH₂CH₂, Y′=O, X′=CH₂CH₂; Y′=OC(O), R=4-F-phenyl X′=CH₂CH₂, Y′=OC(O), R=2,6-difluorophenyl X′=CH₂CH₂, Y′=OC(O), R=4-nitrophenyl X′=CH₂CH₂, Y′=OC(O), R=t-Bu X′=CH₂CH₂, Y′=OC(O), R=cyclopropyl X′=CH₂CH₂, Y′=OC(O), R=Me X′=CH₂CH₂CH₂, Y′=O, R=H X′=-, Y′=S(O), R=4-bromobenzyl X′=CH₂, Y′=S, R=Me X′=CH₂, Y′=S(O), R=Me X′=CH₂, Y′=S(O)₂, R=t-Bu X′=CH₂, Y′=S, R=2-thienyl X′=CH₂CH₂, Y′=S, R=Me X′=CH₂CH₂, Y′=S, R=n-Pr X′=CH₂CH₂, Y′=S, R=benzyl X′=CH₂CH₂, Y′=S, R=2-thienylmethyl X′=CH₂CH₂CH₂, Y′=S, R=Me X′=CH₂CH₂CH₂, Y′=SO, R=Me X′=CH₂CH₂CH₂CH₂, Y′=S, R=CH₂CH₂CH₂CH₂OMe are not included.
 2. The 4-trifluoromethyl-3-oxadiazolylpyridine as claimed in claim 1, wherein m in the formula (I′) is
 0. 3. The 4-trifluoromethyl-3-oxadiazolylpyridine as claimed in claim 1, wherein X′ in the formula (I′) is a single bond, —CH₂—, —CH₂—CH₂—, —CH₂—CH(CH₃)— or —CH₂—C(CH₃)₂—.
 4. The 4-trifluoromethyl-3-oxadiazolylpyridine as claimed in claim 1, wherein Y′ in the formula (I′) is —O—, —S—, —SO—, —SO₂—, —O—CO—, —O—CO—O—, —O—CO—NR⁶—, —SO₂—NR⁷—, —O—SO₂— or —SO₂—O—.
 5. A process for preparing a compound of the formula (I′) as claimed in claim 1, comprising reacting an activated derivative of an acid of the formula (II),

in the presence of a base with a compound of the formula (III),

in which the radical —X′—Y′—R is as defined in formula (I′), or is a precursor of a radical defined therein.
 6. A composition having insecticidal, acaricidal and/or nematicidal action, which comprises at least one compound as claimed in claim
 1. 7. The composition as claimed in claim 6, further comprising a carrier substance and/or a surface-active substance.
 8. The composition as claimed in claim 6, further comprising an active compound from the group of acaricides, fungicides, herbicides, insecticides, nematicides or growth-regulating substances.
 9. A veterinary composition for treatment of a patient in need thereof, comprising the compound of claim 1 or the composition of claim
 6. 10. A method for controlling harmful insects, acarids and nematodes, which comprises applying an effective amount of the compound as claimed in claim 1 or the composition as claimed in claim 6 to the site of the desired action.
 11. A method for protecting useful plants against the undesirable action of harmful insects, acarids and nematodes, which comprises treating the seed of the useful plant with at least one compound as claimed in claim 1 or at least one composition as claimed in claim
 6. 12. A method of controlling harmful insects, acarids and nematodes in useful plants, comprising applying an effective amount of the compound of claim 1 or the composition of claim 6 to said useful plant. 